Enantiospecific and regioselective rhodium-catalyzed allylic alkylation: Diastereoselective approach to quaternary carbon stereogenic centers

被引：54

作者：

Evans, PA ^{[1
]}

Kennedy, LJ ^{[1
]}

机构：

[1] Univ Delaware, Dept Chem & Biochem, Brown Lab, Newark, DE 19716 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 15期

关键词：

D O I：

10.1021/ol005953g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The enantiospecific and regioselective rhodium-catalyzed allylic alkylation of a series of chiral nonracemic allylic carbonates, followed by ozonolysis and reductive lactonization, provides a convenient route to optically active gamma-lactones, Sequential alkylation and reductive alkylation furnished the alpha-quaternary-beta-ternary substituted gamma-lactone derivative as a greater than or equal to 10:1 mixture of diastereoisomers.

引用

页码：2213 / 2215

页数：3

共 20 条

[1]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[2]

Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO

[3]

2-V

[4] Conservation of absolute configuration in the acyclic rhodium-catalyzed allylic alkylation reaction:: Evidence for an enyl (σ+π) organorhodium intermediate [J].

Evans, PA ;

Nelson, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) :5581-5582

[5] Regioselective and enantiospecific rhodium-catalyzed intermolecular allylic etherification with ortho-substituted phenols [J].

Evans, PA ;

Leahy, DK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :5012-5013

[6] Regioselective rhodium-catalyzed allylic alkylation with a modified Wilkinson's catalyst [J].

Evans, PA ;

Nelson, JD .

TETRAHEDRON LETTERS, 1998, 39 (13) :1725-1728

[7] Enantiospecific synthesis of allylamines via the regioselective rhodium-catalyzed allylic amination reaction [J].

Evans, PA ;

Robinson, JE ;

Nelson, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6761-6762

[8] Regioselective Rh-catalyzed allylic amination/ring-closing metathesis approach to monocyclic azacycles: Diastereospecific construction of 2,5-disubstituted pyrrolines [J].

Evans, PA ;

Robinson, JE .

ORGANIC LETTERS, 1999, 1 (12) :1929-1931

[9] SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION [J].

FROST, CG ;

HOWARTH, J ;

WILLIAMS, JMJ .

TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1089-1122

[10] ASYMMETRIC CREATION OF QUATERNARY CARBON CENTERS [J].

FUJI, K .

CHEMICAL REVIEWS, 1993, 93 (06) :2037-2066

← 1 2 →