Scope and limitations in the Jacobsen epoxidation of dienyl sulfones

被引：39

作者：

Hentemann, MF ^{[1
]}

Fuchs, PL ^{[1
]}

机构：

[1] PURDUE UNIV,DEPT CHEM,W LAFAYETTE,IN 47907

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 32期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)01275-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Symchiral (salen)Mn(lll)CI complexes catalyze the epoxidation of 2-sulfonyl, 1,3 cyclic dienes with exceptional enantioselectivity. The incorporation of the sulfone moiety increases the enantioselectivity by up to 30%, relative to the unsubstituted cyclic 1,3-diene. (C) 1997 Elsevier Science Ltd.

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页码：5615 / 5618

页数：4

相关论文

共 21 条

[1]

BACKVALL JE, 1987, J AM CHEM SOC, V109, P6396

[2]

BACKVALL JE, 1988, J ORG CHEM, V53, P2398

[3] HIGHLY ENANTIOSELECTIVE, CATALYTIC EPOXIDATION OF TRISUBSTITUTED OLEFINS [J].

BRANDES, BD ;

JACOBSEN, EN .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16) :4378-4380

[4] ENANTIOSELECTIVE EPOXIDATION OF CYCLIC 1,3-DIENES CATALYZED BY A STERICALLY AND ELECTRONICALLY OPTIMIZED (SALEN)MN COMPLEX [J].

CHANG, S ;

HEID, RM ;

JACOBSEN, EN .

TETRAHEDRON LETTERS, 1994, 35 (05) :669-672

[5] MECHANISTIC STUDY OF A SYNTHETICALLY USEFUL MONOOXYGENASE MODEL USING THE HYPERSENSITIVE PROBE TRANS-2-PHENYL-1-VINYLCYCLOPROPANE [J].

FU, H ;

LOOK, GC ;

ZHANG, W ;

JACOBSEN, EN ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6497-6500

[6]

HAMADA T, 1994, SYNLETT, P479

[7] RATIONAL DESIGN OF MN-SALEN EPOXIDATION CATALYSTS - PRELIMINARY-RESULTS [J].

HOSOYA, N ;

HATAYAMA, A ;

IRIE, R ;

SASAKI, H ;

KATSUKI, T .

TETRAHEDRON, 1994, 50 (15) :4311-4322

[8]

HOSOYA N, 1993, SYNLETT, P641

[9] CATALYTIC ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED OLEFINS USING CHIRAL (SALEN)MANGANESE(III) COMPLEXES [J].

IRIE, R ;

NODA, K ;

ITO, Y ;

MATSUMOTO, N ;

KATSUKI, T .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :481-494

[10] ELECTRONIC TUNING OF ASYMMETRIC CATALYSTS [J].

JACOBSEN, EN ;

ZHANG, W ;

GULER, ML .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) :6703-6704