Enantioselective synthesis of α-amino acetals (aldehydes) via nucleophilic 1,2-addition to chiral 1,3-oxazolidines
A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines 4 is described. Chemical yields and diastereoselectivities are generally excellent (91–100% de). The resulting amino alcohols 6 may be oxidati...
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| Published in | Tetrahedron letters Vol. 35; no. 41; pp. 7489 - 7492 |
|---|---|
| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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OXFORD
Elsevier Ltd
10.10.1994
Elsevier |
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| Abstract | A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines
4 is described. Chemical yields and diastereoselectivities are generally excellent (91–100% de). The resulting amino alcohols
6 may be oxidatively or reductively cleaved to enantiomerically enriched α-amino acetals
3 which are useful chiral building blocks.
Treatment of the oxazolidines
1 with Grignard reagents afforded the aminoalcohols
2 in good yields and high stereoselectivity. |
|---|---|
| AbstractList | A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines
4 is described. Chemical yields and diastereoselectivities are generally excellent (91–100% de). The resulting amino alcohols
6 may be oxidatively or reductively cleaved to enantiomerically enriched α-amino acetals
3 which are useful chiral building blocks.
Treatment of the oxazolidines
1 with Grignard reagents afforded the aminoalcohols
2 in good yields and high stereoselectivity. A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines 4 is described. Chemical yields and diastereoselectivities are generally excellent (91-100% de). The resulting amino alcohols 6 may be oxidatively or reductively cleaved to enantiomerically enriched alpha-amino acetals 3 which are useful chiral building blocks. |
| Author | Muralidharan, K.Raman Mokhallalati, Mohamed K. Pridgen, Lendon N. |
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| Cites_doi | 10.1080/00304949009356309 10.1248/cpb.34.2071 10.1055/s-1993-22456 10.1246/cl.1989.901 10.1055/s-1990-21195 10.1016/S0040-4039(00)73330-2 10.1016/S0040-4039(00)60054-0 10.1021/jo00003a087 10.1021/jo00030a035 10.1021/cr00091a004 10.1016/S0040-4039(00)61180-2 10.1021/jo00065a020 |
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| References | Pridgen, Mokhallalati, Wu (BIB4) 1992; 57 Enders, Funk, Klatt, Raabe, Havestrevdt (BIB10) 1993; 32 Denmark, Nicaise (BIB9) 1993 Wu, Pridgen (BIB1) 1991; 56 Takahashi, Chida, Yoshi, Suzuki, Yanaura (BIB6) 1986; 34 Merger, Frank (BIB11) 1989; 111 Mokhallalati, Muralidharan, Pridgen (BIB5) 1994; 35 Mokhallalati, Wu, Pridgen (BIB3) 1993; 34 Jurczak, Golebiowski, Fisher, Muchowski (BIB7) 1989; 89 BIB12 Kametani, Kondoh, Honda, Ishizone, Suzuki, Mori (BIB13) 1989 McKennon, Meyers (BIB14) 1993; 58 Wu, Pridgen (BIB2) 1990 Leanna, Sowin, Morton (BIB8) 1992; 33 FISHER, LE (WOS:A1990DK44000001) 1990; 22 ENDERS, D (WOS:A1993KW50100023) 1993; 32 JURCZAK, J (WOS:A1989T169000004) 1989; 89 DENMARK, SE (WOS:A1993LD37500016) 1993 MCKENNON, MJ (WOS:A1993LU65300020) 1993; 58 KAMETANI, T (WOS:A1989U756400054) 1989 (WOS:A1994PL49600001.1) 1989 PRIDGEN, LN (WOS:A1992HE09000035) 1992; 57 MOKHALLALATI, MK (WOS:A1993KE37100009) 1993; 34 TAKAHASHI, H (WOS:A1986C741200030) 1986; 34 MOKHALLALATI, MK (WOS:A1994NT65500001) 1994; 35 LEANNA, MR (WOS:A1992JK74300007) 1992; 33 WU, MJ (WOS:A1990EC13200030) 1990 WU, MJ (WOS:A1991EW18200087) 1991; 56 Enders (10.1016/S0040-4039(00)78325-0_BIB10) 1993; 32 Merger (10.1016/S0040-4039(00)78325-0_BIB11) 1989; 111 Takahashi (10.1016/S0040-4039(00)78325-0_BIB6) 1986; 34 Denmark (10.1016/S0040-4039(00)78325-0_BIB9) 1993 Mokhallalati (10.1016/S0040-4039(00)78325-0_BIB5) 1994; 35 Mokhallalati (10.1016/S0040-4039(00)78325-0_BIB3) 1993; 34 McKennon (10.1016/S0040-4039(00)78325-0_BIB14) 1993; 58 Pridgen (10.1016/S0040-4039(00)78325-0_BIB4) 1992; 57 Wu (10.1016/S0040-4039(00)78325-0_BIB1) 1991; 56 Jurczak (10.1016/S0040-4039(00)78325-0_BIB7_1) 1989; 89 Wu (10.1016/S0040-4039(00)78325-0_BIB2) 1990 Fisher (10.1016/S0040-4039(00)78325-0_BIB7_2) 1990; 22 Kametani (10.1016/S0040-4039(00)78325-0_BIB13) 1989 Leanna (10.1016/S0040-4039(00)78325-0_BIB8) 1992; 33 |
| References_xml | – volume: 35 start-page: 4267 year: 1994 ident: BIB5 publication-title: Tetrahedron Lett. contributor: fullname: Pridgen – volume: 56 start-page: 1340 year: 1991 ident: BIB1 publication-title: J. Org. Chem. contributor: fullname: Pridgen – start-page: 636 year: 1990 ident: BIB2 publication-title: Synlett. contributor: fullname: Pridgen – volume: 32 start-page: 418 year: 1993 ident: BIB10 publication-title: Angew. Chem. contributor: fullname: Havestrevdt – volume: 34 start-page: 2071 year: 1986 ident: BIB6 publication-title: Chem. Pharm. Bull. contributor: fullname: Yanaura – volume: 57 start-page: 1237 year: 1992 ident: BIB4 publication-title: J. Org. Chem. contributor: fullname: Wu – volume: 58 start-page: 3568 year: 1993 ident: BIB14 publication-title: J. Org. Chem. contributor: fullname: Meyers – volume: 111 start-page: 232838t year: 1989 ident: BIB11 publication-title: Chem. 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SYNTHESIS AND ANALGESIC ACTIVITY OF OPTICALLY PURE (R)-N-ALKYL-1-CYCLOHEYXL-2-PHENYLETHYLAMINES AND (S)-N-ALKYL-1-CYCLOHEXYL-2-PHENYLETHYLAMINES publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: TAKAHASHI, H – volume: 56 start-page: 1340 year: 1991 ident: WOS:A1991EW18200087 article-title: SYNTHESIS OF CHIRAL ALPHA-ALKYL PHENETHYLAMINES VIA ORGANOMETALLIC ADDITION TO CHIRAL 2-ARYL-1,3-OXAZOLIDINES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: WU, MJ – volume: 58 start-page: 3568 year: 1993 ident: WOS:A1993LU65300020 article-title: A CONVENIENT REDUCTION OF AMINO-ACIDS AND THEIR DERIVATIVES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: MCKENNON, MJ – volume: 22 start-page: 399 year: 1990 ident: WOS:A1990DK44000001 article-title: SYNTHESIS OF ALPHA-AMINOALDEHYDES AND ALPHA-AMINOKETONES - A REVIEW publication-title: ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL contributor: fullname: FISHER, LE – volume: 89 start-page: 149 year: 1989 ident: WOS:A1989T169000004 article-title: OPTICALLY-ACTIVE N-PROTECTED ALPHA-AMINO ALDEHYDES IN ORGANIC-SYNTHESIS publication-title: CHEMICAL REVIEWS contributor: fullname: JURCZAK, J – volume: 22 start-page: 399 year: 1990 ident: 10.1016/S0040-4039(00)78325-0_BIB7_2 publication-title: Org. 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| Snippet | A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines
4... A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines 4... |
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| Title | Enantioselective synthesis of α-amino acetals (aldehydes) via nucleophilic 1,2-addition to chiral 1,3-oxazolidines |
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