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
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机构:TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,TOYAMA 93001,JAPAN
ARAI, Y
MATSUI, M
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MATSUI, M
FUJII, A
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FUJII, A
KONTANI, T
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KONTANI, T
OHNO, T
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OHNO, T
KOIZUMI, T
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KOIZUMI, T
SHIRO, M
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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.