DIASTEREOSELECTIVE DIELS-ALDER CYCLOADDITIONS WITH CHIRAL 1-(ALKYLSULFINYL)-2-NITROALKENES

被引:25
作者
FUJI, K
TANAKA, K
ABE, H
MATSUMOTO, K
HARAYAMA, T
IKEDA, A
TAGA, T
MIWA, Y
NODE, M
机构
[1] OKAYAMA UNIV,FAC PHARMACEUT SCI,OKAYAMA 700,JAPAN
[2] KYOTO UNIV,GRAD SCH HUMAN & ENVIRONM STUDIES,SAKYO KU,KYOTO 606,JAPAN
[3] KYOTO UNIV,FAC PHARMACEUT SCI,SAKYO KU,KYOTO 606,JAPAN
[4] KYOTO PHARMACEUT UNIV,YAMASHINA KU,KYOTO 607,JAPAN
关键词
D O I
10.1021/jo00087a043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several chiral 2-nitro-1-sulfinylalkenes were prepared and examined for their utility as dienophiles for asymmetric [4 + 2] cycloaddition. Trisubstituted dienophiles 3-6 undergo diastereoselective cycloaddition with cyclopentadiene in the presence of Lewis acids. Even the tetrasubstituted chiral sulfinyl dienophiles 1 and 2 could be coerced into undergoing [4 + 2] cycloaddition to afford the cycloadducts in high yield without concomitant elimination if the reaction was conducted under high pressure. Generally, the Z-sulfinyl dienophiles 1-4 showed higher diastereo- and endo/exo-selectivity than;the E-dienophiles 5 and 6.
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收藏
页码:2211 / 2218
页数:8
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