Stereoselective conjugate addition of carbon nucleophiles to chiral (E)-nitroalkenes bearing a gamma-stereocenter. Origins of the observed anti selectivity.

被引：17

作者：

Ayerbe, M

Morao, I

Arrieta, A

Linden, A

Cossio, FP

机构：

[1] EUSKAL HERRIKO UNIBERTSITATEA,KIMIKA FAK,E-20080 SAN SEBASTIAN,SPAIN

[2] UNIV ZURICH,INST INORGAN CHEM,CH-8057 ZURICH,SWITZERLAND

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 17期

关键词：

D O I：

10.1016/0040-4039(96)00468-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction between different organometallic carbon nucleophiles and chiral (E)-nitroalkenes has been studied. Anti selectivities have been observed in all cases. SCF-MO calculations suggest that the observed stereocontrol relies on the anti disposition of a donor group (methyl or hydrogen) with respect to the C-C bond in formation. (C) 1996 Elsevier Science Ltd.

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页码：3055 / 3058

页数：4

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共 22 条

[1] OPTIMIZATION AND APPLICATION OF LITHIUM PARAMETERS FOR PM3 [J].

ANDERS, E ;

KOCH, R ;

FREUNSCHT, P .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1993, 14 (11) :1301-1312

[2] 4M LITHIUM PERCHLORATE-NITROMETHANE - AN EFFICIENT SOLVENT IN DIELS-ALDER REACTIONS USING NITROALKENES AS DIENOPHILES [J].

AYERBE, M ;

COSSIO, FP .

TETRAHEDRON LETTERS, 1995, 36 (25) :4447-4450

[3] (PHENYLTHIO)NITROMETHANE IN THE TOTAL SYNTHESIS OF POLYOXIN-C [J].

BARRETT, AGM ;

LEBOLD, SA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3853-3857

[4] 1,2-ASYMMETRIC INDUCTION IN CONJUGATE ADDITIONS TO NITROALKENES [J].

BARRETT, AGM ;

RYS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (08) :1009-1017

[5] CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].

BARRETT, AGM ;

GRABOSKI, GG .

CHEMICAL REVIEWS, 1986, 86 (05) :751-762

[6] CERIUM(III) CHLORIDE MEDIATED MICHAEL ADDITION OF RMGX TO NITROENES - A VERY EFFICIENT ACCESS TO COMPLEX NITROALKANES [J].

BARTOLI, G ;

BOSCO, M ;

SAMBRI, L ;

MARCANTONI, E .

TETRAHEDRON LETTERS, 1994, 35 (46) :8651-8654

[7] 1,4-ADDITION TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BEARING A GAMMA-STEREOCENTER - A MOLECULAR MECHANICS MODEL FOR STERIC INTERACTIONS IN THE TRANSITION-STATE [J].

BERNARDI, A ;

CAPELLI, AM ;

GENNARI, C ;

SCOLASTICO, C .

TETRAHEDRON-ASYMMETRY, 1990, 1 (01) :21-32

[8] REVERSAL OF PI-FACIAL DIASTEREOSELECTION UPON ELECTRONEGATIVE SUBSTITUTION OF THE SUBSTRATE AND THE REAGENT [J].

CIEPLAK, AS ;

TAIT, BD ;

JOHNSON, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) :8447-8462

[9] STEREOSELECTIVITY OF THE NUCLEOPHILIC-ADDITION OF ORGANOCOPPER REAGENTS TO CHIRAL ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS - ABINITIO MOLECULAR-ORBITAL STUDIES OF STERIC AND ELECTRONIC EFFECTS [J].

DORIGO, AE ;

MOROKUMA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6524-6536

[10] THEORETICAL-STUDIES OF NUCLEOPHILIC ADDITIONS OF ORGANOCOPPER REAGENTS TO ACROLEIN - RATIONALIZATION OF THE DIFFERENCES IN REGIOSELECTIVITY IN THE REACTIONS OF METHYLCOPPER AND METHYLLITHIUM [J].

DORIGO, AE ;

MOROKUMA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4635-4643