HETERODIENE CYCLOADDITIONS OF C-2 SYMMETRICAL 4,5-DISUBSTITUTED KETENE ACETALS - THE NETT ASYMMETRIC CONJUGATE ADDITION OF RECYCLABLE ACETIC ESTER ENOLATE EQUIVALENTS TO AN ACTIVATED ENONE

被引：37

作者：

WALLACE, TW ^{[1
]}

WARDELL, I ^{[1
]}

LI, KD ^{[1
]}

LEEMING, P ^{[1
]}

REDHOUSE, AD ^{[1
]}

CHALLAND, SR ^{[1
]}

机构：

[1] WELLCOME RES LABS,BECKENHAM BR3 3BS,KENT,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 18期

关键词：

D O I：

10.1039/p19950002293

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heterodiene cycloadditions of 3-formylchromone 2 to a series of ketene acetals 1 derived from C-2 symmetric 1,2-diarylethane-1,2-diols are diastereoselective. From (S,S)-1,2-di(o-tolyl)ethane-1,2-diol 6c the major cycloadduct 3c was isolated by crystallisation and transformed by acid-catalysed methanolysis into (S)methyl 4-oxo-3,4-dihydro-2H-1-benzopyran-2-ylacetate 5, together with the original 1,2-diol 6c which could be recycled. The structures of two cyclic carbonates 22a and 22c were determined by X-ray diffraction and used as models in seeking a mechanistic rationale for the stereoselective cycloadditions of the analogous ketene acetals 1a and 1c.

引用

页码：2293 / 2308

页数：16

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[1] SYNTHESES AND CRYSTAL-STRUCTURES OF THE CINCHONA ALKALOID DERIVATIVES USED AS LIGANDS IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].