First enantioselective synthesis of (+)-(3R,3aS,6aS)-3-hydroxy-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one -: a versatile chiral heterocyclic building block

被引：20

作者：

Kudis, S ^{[1
]}

Helmchen, G ^{[1
]}

机构：

[1] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany

来源：

TETRAHEDRON | 1998年 / 54卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(98)00497-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric Pd-catalyzed allylic alkylations of 2-acetoxymalonates with 2-cyclopentenyl chloride are described. With the cymantrene based phosphinooxazoline 2 as chiral ligand enantiomeric excess of > 99% and > 90% yield were obtained. Alkylation products were transformed in three steps to (+)-(3R,3aS. 6aS)-3-hydroxy-3, 3a, 4, 6a-tetrahydrocyclopenta[b]furan-2-one (1a) in up to 52% yield (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：10449 / 10456

页数：8

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