Carboxy mediated stereoselective reduction of ketones with sodium triacetoxyborohydride: synthesis of novel 3,4-fused tetrahydropyran and tetrahydrofuran prolines

Graphic In the presence of a carboxyl group positioned for participation, NaBH(OAc) 3 will reduce the usually unreactive ketones in a stereoselective manner. This reaction was applied in a key step to prepare precursors 7 and 15 toward the title compounds 1 and 2 . These results are consistent with...

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Published inTetrahedron letters Vol. 45; no. 32; pp. 6097 - 6100
Main Authors Liu, Yi-Tsung, Wong, Jesse K., Tao, Meng, Osterman, Rebecca, Sannigrahi, Mousumi, Girijavallabhan, Viyyoor M., Saksena, Anil
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.08.2004
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Sodium triacetoxyborohydride
Stereoselective reduction
Tetrahydropyran and tetrahydrofuran proline
Sodium triacetoxyborohydride
Stereoselective reduction
Tetrahydropyran and tetrahydrofuran proline
tetrahydropyran and tetrahydrofuran proline
stereoselective reduction
sodium triacetoxyborohydride
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Abstract Graphic In the presence of a carboxyl group positioned for participation, NaBH(OAc) 3 will reduce the usually unreactive ketones in a stereoselective manner. This reaction was applied in a key step to prepare precursors 7 and 15 toward the title compounds 1 and 2 . These results are consistent with the exchange of one of the acetoxy groups in the reducing agent with the carboxy group followed by intramolecular delivery of the hydride.
AbstractList In the presence of a carboxyl group positioned for participation, NaBH(OAc)(3) will reduce the usually unreactive ketones in a stereoselective manner. This reaction was applied in a key step to prepare precursors 7 and 15 toward the title compounds 1 and 2. These results are consistent with the exchange of one of the acetoxy groups in the reducing agent with the carboxy group followed by intramolecular delivery of the hydride. (C) 2004 Elsevier Ltd. All rights reserved.
Graphic In the presence of a carboxyl group positioned for participation, NaBH(OAc) 3 will reduce the usually unreactive ketones in a stereoselective manner. This reaction was applied in a key step to prepare precursors 7 and 15 toward the title compounds 1 and 2 . These results are consistent with the exchange of one of the acetoxy groups in the reducing agent with the carboxy group followed by intramolecular delivery of the hydride.
Author Tao, Meng
Girijavallabhan, Viyyoor M.
Liu, Yi-Tsung
Sannigrahi, Mousumi
Saksena, Anil
Wong, Jesse K.
Osterman, Rebecca
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crossref_primary_10_1002_chin_200445203
crossref_primary_10_2174_1570179421666230821102745
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Cites_doi 10.1016/S0040-4039(03)00663-4
10.1021/jo034214l
10.1016/S0165-6147(00)88980-4
10.1002/1521-3773(20020503)41:9<1600::AID-ANIE1600>3.0.CO;2-V
10.1016/S0040-4039(00)81383-0
10.1021/jm00105a068
10.1021/jo9618738
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Issue 32
Keywords Sodium triacetoxyborohydride
Stereoselective reduction
Tetrahydropyran and tetrahydrofuran proline
tetrahydropyran and tetrahydrofuran proline
stereoselective reduction
sodium triacetoxyborohydride
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References Kergomard (BIB6) 1957; 9
Saksena, Mangiaracina, Evans, Chapman, Carriera (BIB4) 1983; 24
West, Fairlie (BIB2) 1995; 16
BIB7
Holladay, Lin, May, Garvey, Witte, Miller, Wolfram, Nadzan (BIB3) 1991
BIB5
Beausoleil, L'Archeveque, Belec, Atfani, Lubell, Del Valle, Goodman, Del Valle, Goodman, Trabocchi, Cini, Menchi, Guarna (BIB1) 1996; 61
De Valle, JR (WOS:000175568900033) 2002; 41
Del Valle, JR (WOS:000182825000024) 2003; 68
HOLLADAY, MW (WOS:A1991ET54500068) 1991; 34
Beausoleil, E (WOS:A1996WC12000056) 1996; 61
SAKSENA, AK (WOS:A1983PY03600013) 1983; 24
WEST, ML (WOS:A1995QP89200008) 1995; 16
Trabocchi, A (WOS:000182267000012) 2003; 44
EVANS, DA (WOS:A1988N634100035) 1988; 110
KERGOMARD, A (WOS:A1957WN24700045) 1957
Beausoleil (10.1016/j.tetlet.2004.06.070_BIB1_1) 1996; 61
Del Valle (10.1016/j.tetlet.2004.06.070_BIB1_3) 2002; 41
Saksena (10.1016/j.tetlet.2004.06.070_BIB4_1) 1983; 24
Del Valle (10.1016/j.tetlet.2004.06.070_BIB1_2) 2003; 68
West (10.1016/j.tetlet.2004.06.070_BIB2) 1995; 16
Holladay (10.1016/j.tetlet.2004.06.070_BIB3) 1991
Evans (10.1016/j.tetlet.2004.06.070_BIB4_2) 1988; 110
Kergomard (10.1016/j.tetlet.2004.06.070_BIB6) 1957; 9
Trabocchi (10.1016/j.tetlet.2004.06.070_BIB1_4) 2003; 44
References_xml – ident: BIB7
– ident: BIB5
– volume: 61
  start-page: 9447
  year: 1996
  end-page: 9454
  ident: BIB1
  publication-title: J. Org. Chem.
  contributor:
    fullname: Guarna
– start-page: 455
  year: 1991
  end-page: 457
  ident: BIB3
  publication-title: J. Med. Chem.
  contributor:
    fullname: Nadzan
– volume: 24
  start-page: 273
  year: 1983
  end-page: 276
  ident: BIB4
  publication-title: Tetrahedron Lett.
  contributor:
    fullname: Carriera
– volume: 9
  start-page: 1161
  year: 1957
  end-page: 1166
  ident: BIB6
  publication-title: Bull. Soc. Chim. Fr.
  contributor:
    fullname: Kergomard
– volume: 16
  start-page: 67
  year: 1995
  end-page: 75
  ident: BIB2
  publication-title: Trends Pharm. Sci.
  contributor:
    fullname: Fairlie
– volume: 61
  start-page: 9447
  year: 1996
  ident: WOS:A1996WC12000056
  article-title: 5-tert-butylproline
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  contributor:
    fullname: Beausoleil, E
– volume: 44
  start-page: 3489
  year: 2003
  ident: WOS:000182267000012
  article-title: A new bicyclic proline-mimetic amino acid
  publication-title: TETRAHEDRON LETTERS
  doi: 10.1016/S0040-4039(03)00663-4
  contributor:
    fullname: Trabocchi, A
– volume: 16
  start-page: 67
  year: 1995
  ident: WOS:A1995QP89200008
  article-title: TARGETING HIV-1 PROTEASE - A TEST OF DRUG-DESIGN METHODOLOGIES
  publication-title: TRENDS IN PHARMACOLOGICAL SCIENCES
  contributor:
    fullname: WEST, ML
– volume: 110
  start-page: 3560
  year: 1988
  ident: WOS:A1988N634100035
  article-title: DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE
  publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
  contributor:
    fullname: EVANS, DA
– volume: 24
  start-page: 273
  year: 1983
  ident: WOS:A1983PY03600013
  article-title: RECENT STUDIES ON VERATRUM ALKALOIDS - A NEW REACTION OF SODIUM TRIACETOXYBOROHYDRIDE [NABH(OAC)3]
  publication-title: TETRAHEDRON LETTERS
  contributor:
    fullname: SAKSENA, AK
– start-page: 1161
  year: 1957
  ident: WOS:A1957WN24700045
  article-title: SUR LES REACTIONS DES DERIVES DES PINENES-ALPHA ET PINENES-BETA AYANT UNE FONCTION ALCOOL EN ALPHA DU CYCLE BUTANIQUE
  publication-title: BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE
  contributor:
    fullname: KERGOMARD, A
– volume: 41
  start-page: 1600
  year: 2002
  ident: WOS:000175568900033
  article-title: Stereoselective synthesis of Boc-protected cis and trans-4-trifluoromethylprolines by asymmetric hydrogenation reactions
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
  contributor:
    fullname: De Valle, JR
– volume: 68
  start-page: 3923
  year: 2003
  ident: WOS:000182825000024
  article-title: Asymmetric hydrogenations for the synthesis of Boc-protected 4-alkylprolinols and prolines
  publication-title: JOURNAL OF ORGANIC CHEMISTRY
  doi: 10.1021/jo034214l
  contributor:
    fullname: Del Valle, JR
– volume: 34
  start-page: 455
  year: 1991
  ident: WOS:A1991ET54500068
  article-title: TRANS-3-NORMAL-PROPYL-L-PROLINE IS A HIGHLY FAVORABLE, CONFORMATIONALLY RESTRICTED REPLACEMENT FOR METHIONINE IN THE C-TERMINAL TETRAPEPTIDE OF CHOLECYSTOKININ - STEREOSELECTIVE SYNTHESIS OF 3-ALLYL-L-PROLINE AND 3-NORMAL-PROPYL-L-PROLINE DERIVATIVES FROM 4-HYDROXY-L-PROLINE
  publication-title: JOURNAL OF MEDICINAL CHEMISTRY
  contributor:
    fullname: HOLLADAY, MW
– volume: 44
  start-page: 3489
  year: 2003
  ident: 10.1016/j.tetlet.2004.06.070_BIB1_4
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(03)00663-4
  contributor:
    fullname: Trabocchi
– volume: 16
  start-page: 67
  year: 1995
  ident: 10.1016/j.tetlet.2004.06.070_BIB2
  publication-title: Trends Pharm. Sci.
  doi: 10.1016/S0165-6147(00)88980-4
  contributor:
    fullname: West
– volume: 68
  start-page: 3923
  year: 2003
  ident: 10.1016/j.tetlet.2004.06.070_BIB1_2
  publication-title: J. Org. Chem.
  doi: 10.1021/jo034214l
  contributor:
    fullname: Del Valle
– volume: 41
  start-page: 1600
  issue: 9
  year: 2002
  ident: 10.1016/j.tetlet.2004.06.070_BIB1_3
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/1521-3773(20020503)41:9<1600::AID-ANIE1600>3.0.CO;2-V
  contributor:
    fullname: Del Valle
– volume: 24
  start-page: 273
  year: 1983
  ident: 10.1016/j.tetlet.2004.06.070_BIB4_1
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(00)81383-0
  contributor:
    fullname: Saksena
– volume: 9
  start-page: 1161
  year: 1957
  ident: 10.1016/j.tetlet.2004.06.070_BIB6
  publication-title: Bull. Soc. Chim. Fr.
  contributor:
    fullname: Kergomard
– start-page: 455
  year: 1991
  ident: 10.1016/j.tetlet.2004.06.070_BIB3
  publication-title: J. Med. Chem.
  doi: 10.1021/jm00105a068
  contributor:
    fullname: Holladay
– volume: 110
  start-page: 560
  year: 1988
  ident: 10.1016/j.tetlet.2004.06.070_BIB4_2
  publication-title: J. Am. Chem. Soc.
  contributor:
    fullname: Evans
– volume: 61
  start-page: 9447
  year: 1996
  ident: 10.1016/j.tetlet.2004.06.070_BIB1_1
  publication-title: J. Org. Chem.
  doi: 10.1021/jo9618738
  contributor:
    fullname: Beausoleil
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Snippet Graphic In the presence of a carboxyl group positioned for participation, NaBH(OAc) 3 will reduce the usually unreactive ketones in a stereoselective manner....
In the presence of a carboxyl group positioned for participation, NaBH(OAc)(3) will reduce the usually unreactive ketones in a stereoselective manner. This...
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SubjectTerms Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Sodium triacetoxyborohydride
Stereoselective reduction
Tetrahydropyran and tetrahydrofuran proline
Title Carboxy mediated stereoselective reduction of ketones with sodium triacetoxyborohydride: synthesis of novel 3,4-fused tetrahydropyran and tetrahydrofuran prolines
URI https://dx.doi.org/10.1016/j.tetlet.2004.06.070
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