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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 08期

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.

引用

页码：2211 / 2218

页数：8

共 44 条

[1] SYNTHESIS AND DIELS-ALDER REACTIONS OF HOMOCHIRAL 2-SULFINYLMALEATES WITH CYCLOPENTADIENE
ALONSO, I
CID, MB
CARRETERO, JC
RUANO, JLG
HOYOS, MA
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (12) : 1193 - 1207
[2] SECONDARY ORBITAL INTERACTIONS DETERMINING REGIOSELECTIVITY IN LEWIS ACID-CATALYZED DIELS-ALDER REACTION .2.
ALSTON, PV
OTTENBRITE, RM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (08) : 1111 - 1116
[3] A NOVEL-APPROACH TO BICYCLIC ALKALOIDS USING A TANDEM DIASTEREOSELECTIVE ACYLIMINOCYCLIZATION AND RETRO DIELS-ALDER REACTION SEQUENCE - SYNTHESIS OF (+)-INDOLIZIDINE AND (+)-LABURNINE
ARAI, Y
KONTANI, T
KOIZUMI, T
[J]. CHEMISTRY LETTERS, 1991, (12) : 2135 - 2138
[4] ARAI Y, 1992, TETRAHEDRON-ASYMMETR, V3, P535
[5] OPTICALLY-ACTIVE 2-PARA-TOLYLSULFINYLACRYLATE - A NOVEL CHIRAL DIENOPHILE WHICH EXHIBITS HIGH REACTIVITY AND DIASTEREOSELECTIVITY
ARAI, Y
KUWAYAMA, S
TAKEUCHI, Y
KOIZUMI, T
[J]. TETRAHEDRON LETTERS, 1985, 26 (50) : 6205 - 6208
[6] POWERFUL DIENOPHILES FOR ASYMMETRIC DIELS-ALDER REACTIONS - ALPHA-(2-EXO-HYDROXY-10-BORNYLSULFINYL)MALEIMIDES
ARAI, Y
MATSUI, M
KOIZUMI, T
SHIRO, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 1983 - 1985
[7] ARAI Y, 1992, REV HETEROATOM CHEM, V6, P202
[8] CATALYSIS OF DIELS-ALDER REACTIONS BY LOW OXIDATION-STATE TRANSITION-METAL LEWIS-ACIDS - FACT AND FICTION
BONNESEN, PV
PUCKETT, CL
HONEYCHUCK, RV
HERSH, WH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) : 6070 - 6081
[9] DIASTEREOSELECTIVE DIELS-ALDER REACTIONS OF OPTICALLY-ACTIVE VINYL SULFOXIDES
BRIMBLE, MA
DAVIS, BR
[J]. TETRAHEDRON, 1985, 41 (21) : 4965 - 4972
[10] CARRUTHERS W, 1990, CYCLOADDITION REACTI, P61

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