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
收藏
页码：10449 / 10456
页数：8
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