ASYMMETRIC DIELS-ALDER REACTION OF OPTICALLY-ACTIVE ALPHA-(2-EXO-HYDROXY-10-BORNYL)SULFINYLMALEIMIDES AND ITS APPLICATION TO OPTICALLY-ACTIVE 5-FUNCTIONALIZED PYRROLINES VIA RETRO-DIELS-ALDER REACTION

被引：34

作者：

ARAI, Y

MATSUI, M

FUJII, A

KONTANI, T

OHNO, T

KOIZUMI, T

SHIRO, M

机构：

[1] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,TOYAMA 93001,JAPAN

[2] RIGAKU CORP,AKISHIMA,TOKYO 196,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 01期

关键词：

D O I：

10.1039/p19940000025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure sulfinylmaleimides 1 have been synthesized. The Diels-Alder reactions of the sulfoxides 1 with various dienes showed high diasteroselectivity. Regioselective reduction of the adducts 4c and 6c followed by desulfinylation afforded the gamma-hydroxy lactams 17 and 27, respectively. N-Acyliminium additions using compounds 17 and 27 proceeded diastereoselectively to give gamma-alkyl lactams 23 and 29 by virtue of its conformationally rigid, bicyclo[2.2.1]- and 7-oxabicyclo[2.2.1]-heptene moiety. respectively. The use of compound 29 allows a simple preparation of chirally 5-functionalised Delta(3)-pyrrolin-2-ones of high optical purity such as compound 25 via retro-Diels-Alder reaction, whereas the thermal cycloreversion of adduct 23 required such forcing conditions as flash vacuum pyrolysis.

引用

页码：25 / 39

页数：15

共 64 条

[1]

ARAI Y, 1990, SYNTHESIS-STUTTGART, P320

[2]

ARAI Y, 1992, CHEM PHARM BULL, V40, P1670

[3] SYNTHESIS AND ASYMMETRIC DIELS-ALDER REACTION OF DIMETHYL (D-ISOBORNEOL-10-SULPHINYL)MALEATE - NOVEL ROUTE TO KEY INTERMEDIATES FOR SYNTHESIS OF SOME CARBOCYCLIC NUCLEOSIDES AND TERPENOIDS [J].