Complementary diastereoselective reduction of cyclic γ-keto acids:: Efficient access to trisubsituted γ-lactones

被引：16

作者：

Bercot, EA ^{[1
]}

Kindrachuk, DE ^{[1
]}

Rovis, T ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 01期

关键词：

D O I：

10.1021/ol047821j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Complementary reduction conditions have been identified that provide ready access to each respective diastereomer of bi- and tricyclic, trisustituted gamma-lactones starting from the corresponding cyclic gamma-keto acids. Subjection of cyclic gamma-keto acids to silane reagents in the presence of trifluoroacetic acid provides all syn-gamma-lactones, while reduction with trialkylborohydrides furnishes the syn,anti-gamma-lactones. The conditions are mild and provide the product lactones in good yields and modest to excellent selectivity.

引用

页码：107 / 110

页数：4

共 43 条

[1] Highly stereoselective aldol reaction for the synthesis of γ-lactones starting from tartaric acid [J].

Barros, MT ;

Burke, AJ ;

Lou, JD ;

Maycock, CD ;

Wahnon, JR .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :7847-7850

[2] A mild and efficient catalytic alkylative monofunctionalization of cyclic anhydrides [J].

Bercot, EA ;

Rovis, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (02) :174-175

[3]

BERCOT EA, IN PRESS J AM CHEM S

[4] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones [J].

Burstein, C ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) :6205-6208

[5] Enantioselective synthesis of paraconic acids [J].

Chhor, RB ;

Nosse, B ;

Sörgel, S ;

Böhn, C ;

Seitz, M ;

Reiser, O .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (01) :260-270

[6] Saturated and unsaturated lactones [J].

Collins, I .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (11) :1377-1395

[7]

Csende F, 2000, HETEROCYCLES, V53, P1379

[8] A general method for the enantioselective synthesis of pantolactone derivatives [J].

Evans, DA ;

Wu, J ;

Masse, CE ;

MacMillan, DWC .

ORGANIC LETTERS, 2002, 4 (20) :3379-3382

[9] Optically pure dihydroxy gamma-alkylated gamma-butyrolactones starting from L-tartaric acid: Application to formal and total syntheses of natural products [J].

Fernandez, AM ;

Plaquevent, JC ;

Duhamel, L .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :4007-4014

[10] Stereochemical control in organic synthesis using silicon-containing compounds [J].

Fleming, I ;

Barbero, A ;

Walter, D .

CHEMICAL REVIEWS, 1997, 97 (06) :2063-2192

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