Stereoselective [2,3]-sigmatropic wittig rearrangement of benzyl ethers derived from vinylcuprate adducts of ( R)-2,3- O-isopropylidenegiyceraldehyde
Allyl alcohols 2 prepared by addition of lithium vinylcuprates to ( R)-2,3- O-isopropylideneglyceraldehyde ( 1) are converted to 3,4,5-trimethoxybenzyl ethers 3 by a one-pot desilylation/alkylation. After deprotonation using potassium t-butoxide/ t-butyllithium/ N, N N′ N′-tetramethylethylenediamine...
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| Published in | Tetrahedron Vol. 51; no. 33; pp. 9023 - 9030 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Elsevier Ltd
14.08.1995
|
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| Abstract | Allyl alcohols
2 prepared by addition of lithium vinylcuprates to (
R)-2,3-
O-isopropylideneglyceraldehyde (
1) are converted to 3,4,5-trimethoxybenzyl ethers
3 by a one-pot desilylation/alkylation. After deprotonation using potassium
t-butoxide/
t-butyllithium/
N,
N N′ N′-tetramethylethylenediamine in
t-butyl methyl ether at −78 °C, substrates
3 undergo a [2,3]-sigmatropic Wittig rearrangement with complete 1,3-chirality transfer and good simple diastereoselectivity to give homoallyl alcohols
5 as the major products. |
|---|---|
| AbstractList | Allyl alcohols
2 prepared by addition of lithium vinylcuprates to (
R)-2,3-
O-isopropylideneglyceraldehyde (
1) are converted to 3,4,5-trimethoxybenzyl ethers
3 by a one-pot desilylation/alkylation. After deprotonation using potassium
t-butoxide/
t-butyllithium/
N,
N N′ N′-tetramethylethylenediamine in
t-butyl methyl ether at −78 °C, substrates
3 undergo a [2,3]-sigmatropic Wittig rearrangement with complete 1,3-chirality transfer and good simple diastereoselectivity to give homoallyl alcohols
5 as the major products. |
| Author | Schoop, Andreas Metz, Peter |
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| Cites_doi | 10.1021/cr00104a001 10.1021/ja00417a060 10.1039/c29700000004 10.1016/S0040-4020(01)81551-9 10.1016/S0040-4039(00)61960-3 10.1135/cccc19880076 10.1016/S0040-4020(01)86212-8 10.1021/jo00184a040 10.1016/S0040-4020(01)88203-X 10.1021/cr00075a011 10.1016/0040-4039(70)80082-X 10.1055/s-1991-26523 10.1016/S0040-4039(00)71351-7 10.1016/S0022-328X(00)84698-7 10.1021/jo00398a013 10.1055/s-1992-21308 10.1021/jo00003a048 10.1246/cl.1982.1643 10.1039/C39920000350 10.1016/S0040-4039(00)97376-3 10.1246/cl.1984.259 10.1021/jo00367a041 10.1021/jo00170a064 10.1021/jo00141a025 |
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| References | Bartlett, Tanzella, Barstow, Daub, Shanklin, Tata, Metz, Mues (bib18) 1982; 47 Rautenstrauch (bib9) 1970 Mikami, Nakai, Brückner, Brückner, Nakai, Mikami (bib4) 1991; Vol. 3 Mikami, Kishi, Nakai (bib8) 1982 Kupchan, Stevens, Rohlfing, Sickles, Sneden, Miller, Bryan, Tomioka, Kawasaki, Iitaka, Koga (bib3) 1978; 43 Schlosser (bib13) 1967; 8 Kishi, Imma, Mikami, Nakai (bib15) 1992 Kende, Liebeskind (bib6) 1976; 98 Keegan, Midland, Werley, McLoughlin, Booker-Milburn, Heffernan, Parsons (bib11) 1991; 56 Snieckus (bib12) 1990; 90 Schlosser, Schlosser, Lochmann, Trekoval (bib10) 1994; 53 Wilson, Georgiadis (bib7) 1983; 48 Sayo, Kitahara, Nakai, Tsai, Midland (bib17) 1984; 49 Metz, Mues, Schoop (bib2) 1992; 48 Ishikawa, Uchiyama, Katsuki, Yamaguchi (bib16) 1990; 31 Metz, Schoop (bib1) 1993; 49 Baldwin, DeBernardis, Patrick (bib14) 1970 Czernecki, Georgoulis, Provelenghiou (bib5) 1976 Schlosser (10.1016/0040-4020(95)00497-V_bib13) 1967; 8 Sayo (10.1016/0040-4020(95)00497-V_bib17_1) 1984 Czernecki (10.1016/0040-4020(95)00497-V_bib5) 1976 Kende (10.1016/0040-4020(95)00497-V_bib6) 1976; 98 Booker-Milburn (10.1016/0040-4020(95)00497-V_bib11_2) 1992 Tsai (10.1016/0040-4020(95)00497-V_bib17_2) 1984; 49 Bartlett (10.1016/0040-4020(95)00497-V_bib18_1) 1982; 47 Brückner (10.1016/0040-4020(95)00497-V_bib4_3) 1991 Lochmann (10.1016/0040-4020(95)00497-V_bib10_3) 1988; 53 Kupchan (10.1016/0040-4020(95)00497-V_bib3_1) 1978; 43 Schlosser (10.1016/0040-4020(95)00497-V_bib10_2) 1992 Metz (10.1016/0040-4020(95)00497-V_bib1) 1993; 49 Metz (10.1016/0040-4020(95)00497-V_bib18_3) 1988; 44 Mikami (10.1016/0040-4020(95)00497-V_bib8) 1982 Brückner (10.1016/0040-4020(95)00497-V_bib4_4) 1991 Snieckus (10.1016/0040-4020(95)00497-V_bib12) 1990; 90 Rautenstrauch (10.1016/0040-4020(95)00497-V_bib9) 1970 Ishikawa (10.1016/0040-4020(95)00497-V_bib16) 1990; 31 (10.1016/0040-4020(95)00497-V_bib4_1) 1991; Vol. 3 Kishi (10.1016/0040-4020(95)00497-V_bib15) 1992 Daub (10.1016/0040-4020(95)00497-V_bib18_2) 1986; 51 Mikami (10.1016/0040-4020(95)00497-V_bib4_2) 1991 Keegan (10.1016/0040-4020(95)00497-V_bib11_1) 1991; 56 Tomioka (10.1016/0040-4020(95)00497-V_bib3_2) 1985; 26 Wilson (10.1016/0040-4020(95)00497-V_bib7) 1983; 48 Baldwin (10.1016/0040-4020(95)00497-V_bib14) 1970 Nakai (10.1016/0040-4020(95)00497-V_bib4_5) 1986; 86 Schlosser (10.1016/0040-4020(95)00497-V_bib10_1) 1994 Metz (10.1016/0040-4020(95)00497-V_bib2) 1992; 48 |
| References_xml | – volume: 8 start-page: 9 year: 1967 end-page: 16 ident: bib13 publication-title: J. Organomet. Chem. contributor: fullname: Schlosser – volume: Vol. 3 start-page: 975 year: 1991 end-page: 1014 ident: bib4 publication-title: Comprehensive Organic Synthesis contributor: fullname: Mikami – start-page: 3535 year: 1976 end-page: 3536 ident: bib5 publication-title: Tetrahedron Lett. contributor: fullname: Provelenghiou – start-page: 189 year: 1992 end-page: 190 ident: bib15 publication-title: Synlett contributor: fullname: Nakai – volume: 49 start-page: 259 year: 1984 end-page: 262 ident: bib17 publication-title: Chem. Lett. contributor: fullname: Midland – volume: 43 start-page: 586 year: 1978 end-page: 590 ident: bib3 publication-title: J. Org. Chem. contributor: fullname: Koga – volume: 48 start-page: 1071 year: 1992 end-page: 1080 ident: bib2 publication-title: Tetrahedron contributor: fullname: Schoop – volume: 49 start-page: 10597 year: 1993 end-page: 10608 ident: bib1 publication-title: Tetrahedron contributor: fullname: Schoop – start-page: 1643 year: 1982 end-page: 1646 ident: bib8 publication-title: Chem. Lett. contributor: fullname: Nakai – volume: 56 start-page: 1185 year: 1991 end-page: 1191 ident: bib11 publication-title: J. Org. Chem. contributor: fullname: Parsons – start-page: 353 year: 1970 end-page: 356 ident: bib14 publication-title: Tetrahedron Lett. contributor: fullname: Patrick – volume: 47 start-page: 3941 year: 1982 end-page: 3945 ident: bib18 publication-title: J. Org. Chem. contributor: fullname: Mues – volume: 53 start-page: 1 year: 1994 end-page: 166 ident: bib10 publication-title: Organometallics in Synthesis: A Manual contributor: fullname: Trekoval – start-page: 4 year: 1970 end-page: 6 ident: bib9 publication-title: J. Chem. Soc., Chem. Commun. contributor: fullname: Rautenstrauch – volume: 31 start-page: 2415 year: 1990 end-page: 2418 ident: bib16 publication-title: Tetrahedron Lett. contributor: fullname: Yamaguchi – volume: 48 start-page: 4143 year: 1983 end-page: 4144 ident: bib7 publication-title: J. Org. Chem. contributor: fullname: Georgiadis – volume: 90 start-page: 879 year: 1990 end-page: 933 ident: bib12 publication-title: Chem. Rev. contributor: fullname: Snieckus – volume: 98 start-page: 267 year: 1976 end-page: 268 ident: bib6 publication-title: J. Am. Chem. Soc. contributor: fullname: Liebeskind – volume: 90 start-page: 879 year: 1990 ident: 10.1016/0040-4020(95)00497-V_bib12 publication-title: Chem. Rev. doi: 10.1021/cr00104a001 contributor: fullname: Snieckus – volume: 98 start-page: 267 year: 1976 ident: 10.1016/0040-4020(95)00497-V_bib6 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00417a060 contributor: fullname: Kende – start-page: 4 year: 1970 ident: 10.1016/0040-4020(95)00497-V_bib9 publication-title: J. Chem. Soc., Chem. Commun. doi: 10.1039/c29700000004 contributor: fullname: Rautenstrauch – volume: 49 start-page: 10597 year: 1993 ident: 10.1016/0040-4020(95)00497-V_bib1 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)81551-9 contributor: fullname: Metz – volume: 26 start-page: 903 year: 1985 ident: 10.1016/0040-4020(95)00497-V_bib3_2 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)61960-3 contributor: fullname: Tomioka – volume: 53 start-page: 76 year: 1988 ident: 10.1016/0040-4020(95)00497-V_bib10_3 publication-title: Collect. Czech. Chem. Commun. doi: 10.1135/cccc19880076 contributor: fullname: Lochmann – volume: 44 start-page: 6841 year: 1988 ident: 10.1016/0040-4020(95)00497-V_bib18_3 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)86212-8 contributor: fullname: Metz – start-page: 3 issue: 2 year: 1991 ident: 10.1016/0040-4020(95)00497-V_bib4_3 publication-title: Kontakte (Darmstadt) contributor: fullname: Brückner – volume: 49 start-page: 1842 year: 1984 ident: 10.1016/0040-4020(95)00497-V_bib17_2 publication-title: J. Org. Chem. doi: 10.1021/jo00184a040 contributor: fullname: Tsai – volume: 48 start-page: 1071 year: 1992 ident: 10.1016/0040-4020(95)00497-V_bib2 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)88203-X contributor: fullname: Metz – volume: Vol. 3 start-page: 975 year: 1991 ident: 10.1016/0040-4020(95)00497-V_bib4_1 – volume: 86 start-page: 885 year: 1986 ident: 10.1016/0040-4020(95)00497-V_bib4_5 publication-title: Chem. Rev. doi: 10.1021/cr00075a011 contributor: fullname: Nakai – start-page: 353 year: 1970 ident: 10.1016/0040-4020(95)00497-V_bib14 publication-title: Tetrahedron Lett. doi: 10.1016/0040-4039(70)80082-X contributor: fullname: Baldwin – start-page: 594 year: 1991 ident: 10.1016/0040-4020(95)00497-V_bib4_2 publication-title: Synthesis doi: 10.1055/s-1991-26523 contributor: fullname: Mikami – start-page: 3535 year: 1976 ident: 10.1016/0040-4020(95)00497-V_bib5 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)71351-7 contributor: fullname: Czernecki – start-page: 227 year: 1992 ident: 10.1016/0040-4020(95)00497-V_bib10_2 contributor: fullname: Schlosser – volume: 8 start-page: 9 year: 1967 ident: 10.1016/0040-4020(95)00497-V_bib13 publication-title: J. Organomet. Chem. doi: 10.1016/S0022-328X(00)84698-7 contributor: fullname: Schlosser – volume: 43 start-page: 586 year: 1978 ident: 10.1016/0040-4020(95)00497-V_bib3_1 publication-title: J. Org. Chem. doi: 10.1021/jo00398a013 contributor: fullname: Kupchan – start-page: 3 issue: 3 year: 1991 ident: 10.1016/0040-4020(95)00497-V_bib4_4 publication-title: Kontakte (Darmstadt) contributor: fullname: Brückner – start-page: 189 year: 1992 ident: 10.1016/0040-4020(95)00497-V_bib15 publication-title: Synlett doi: 10.1055/s-1992-21308 contributor: fullname: Kishi – volume: 56 start-page: 1185 year: 1991 ident: 10.1016/0040-4020(95)00497-V_bib11_1 publication-title: J. Org. Chem. doi: 10.1021/jo00003a048 contributor: fullname: Keegan – start-page: 1643 year: 1982 ident: 10.1016/0040-4020(95)00497-V_bib8 publication-title: Chem. Lett. doi: 10.1246/cl.1982.1643 contributor: fullname: Mikami – start-page: 350 year: 1992 ident: 10.1016/0040-4020(95)00497-V_bib11_2 publication-title: J. Chem. Soc., Chem. Commun. doi: 10.1039/C39920000350 contributor: fullname: Booker-Milburn – volume: 31 start-page: 2415 year: 1990 ident: 10.1016/0040-4020(95)00497-V_bib16 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)97376-3 contributor: fullname: Ishikawa – start-page: 259 year: 1984 ident: 10.1016/0040-4020(95)00497-V_bib17_1 publication-title: Chem. Lett. doi: 10.1246/cl.1984.259 contributor: fullname: Sayo – start-page: 1 year: 1994 ident: 10.1016/0040-4020(95)00497-V_bib10_1 contributor: fullname: Schlosser – volume: 51 start-page: 3402 year: 1986 ident: 10.1016/0040-4020(95)00497-V_bib18_2 publication-title: J. Org. Chem. doi: 10.1021/jo00367a041 contributor: fullname: Daub – volume: 48 start-page: 4143 year: 1983 ident: 10.1016/0040-4020(95)00497-V_bib7 publication-title: J. Org. Chem. doi: 10.1021/jo00170a064 contributor: fullname: Wilson – volume: 47 start-page: 3941 year: 1982 ident: 10.1016/0040-4020(95)00497-V_bib18_1 publication-title: J. Org. Chem. doi: 10.1021/jo00141a025 contributor: fullname: Bartlett |
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| Snippet | Allyl alcohols
2 prepared by addition of lithium vinylcuprates to (
R)-2,3-
O-isopropylideneglyceraldehyde (
1) are converted to 3,4,5-trimethoxybenzyl ethers... |
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| Title | Stereoselective [2,3]-sigmatropic wittig rearrangement of benzyl ethers derived from vinylcuprate adducts of ( R)-2,3- O-isopropylidenegiyceraldehyde |
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