Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution

被引：59

作者：

Breit, B ^{[1
]}

Herber, C ^{[1
]}

机构：

[1] Univ Freiburg, Inst Organ Chem & Biochem, D-79104 Freiburg, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 29期

关键词：

allylation; asymmetric synthesis; diastereoselectivity; organocopper reagents; polyketides;

D O I：

10.1002/anie.200453990

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Can't have too much of a good thing: A flexible, iterative strategy based on a highly selective copper-mediated allylic substitution makes the preparation of any desired oligo(deoxypropionate) stereoisomer possible (see scheme; RDG = reagent-directing group). This approach differs from the established enolate-alkylation methodology through the reversed polarity of the reaction partners and avoids several problems associated with the latter method.

引用

页码：3790 / 3792

页数：3

共 23 条

[1]

Akeboshi T, 2001, ADV SYNTH CATAL, V343, P624, DOI 10.1002/1615-4169(200108)343:6/7<624::AID-ADSC624>3.3.CO

[2]

2-H

[3] MECHANICAL ACTIVATION OF MAGNESIUM TURNINGS FOR THE PREPARATION OF REACTIVE GRIGNARD-REAGENTS [J].

BAKER, KV ;

BROWN, JM ;

HUGHES, N ;

SKARNULIS, AJ ;

SEXTON, A .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :698-703

[4]

BERGER J, 1949, ARCH BIOCHEM, V22, P476

[5] Lipase-based HPLC stationary phase: enantioselective synthesis of 2-substituted 1,3-propanediol monoacetates [J].

Bertucci, C ;

Petri, A ;

Felix, G ;

Perini, B ;

Salvadori, P .

TETRAHEDRON-ASYMMETRY, 1999, 10 (22) :4455-4462

[6] The total synthesis of (+)-pectinatone: An iterative alkylation approach based on the SAMP-hydrazone method [J].

Birkbeck, AA ;

Enders, D .

TETRAHEDRON LETTERS, 1998, 39 (43) :7823-7826

[7] PECTINATONE, A NEW ANTIBIOTIC FROM THE MOLLUSC-SIPHONARIA-PECTINATA [J].

BISKUPIAK, JE ;

IRELAND, CM .

TETRAHEDRON LETTERS, 1983, 24 (30) :3055-3058

[8]

BORNSCHEUER UT, 1999, HYDROLASES ORGANIC S, P70

[9] Stereospecific and stereodivergent construction of quaternary carbon centers through switchable directed/nondirected allylic substitution [J].

Breit, B ;

Demel, P ;

Studte, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3786-3789

[10]

Breit B, 2001, ADV SYNTH CATAL, V343, P429, DOI 10.1002/1615-4169(200107)343:5<429::AID-ADSC429>3.3.CO

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