Asymmetric Diels-Alder reactions with a chiral spirodione, (6S,7S,10R)-7-isopropyl-10-methyl-1-oxaspiro[5.5]undec-3-ene-2,5-dione

被引：8

作者：

Dinesh, CU ^{[1
]}

Kumar, P ^{[1
]}

Reddy, RS ^{[1
]}

Pandey, B ^{[1
]}

Puranik, VG ^{[1
]}

机构：

[1] NATL CHEM LAB,DIV ORGAN CHEM TECHNOL,POONA 411008,MAHARASHTRA,INDIA

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 12期

关键词：

D O I：

10.1016/0957-4166(95)00393-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of the title spirodione, a new class of auxiliary based chiral synthon, using (-)-menthone having a unique carbon-carbon bond is described. Diels-Alder reactions were carried out with variety of dienes using the title auxiliary as a chiral dienophile in the presence of diethyl aluminium chloride as Lewis acid catalyst to afford the cycloadduct with good diastereoselectivity. The configurations of the chiral synthon and cycloadducts were determined by X-ray crystallography. Methodology for detachment of the chiral auxiliary from the cycloadducts has been developed.

引用

页码：2961 / 2970

页数：10

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