TANDEM [4+2]/[3+2]-CYCLOADDITIONS .2. ASYMMETRIC INDUCTION WITH A CHIRAL VINYL ETHER

被引：65

作者：

DENMARK, SE

SENANAYAKE, CBW

HO, GD

机构：

[1] Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana

来源：

TETRAHEDRON | 1990年 / 46卷 / 13-14期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4020(01)85599-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tandem [4+2]/[3+2]-cycloaddition of nitroalkenes tethered to α,β-unsaturated ester dipolarophiles can be effectively triggered with a vinyl ether. Using the chiral vinyl ether 6 as the dienophile, nitroalkenes 1 and 2 undergo highly selective tandem cycloaddition. Hydrogenolytic cleavage of the resulting nitroso acetals produce α-hydroxy lactams (-)-14 and (-)-21 in >98% e.e. with excellent recovery of the chiral auxiliary. The high diastereoselectivity is seen to arise from a strong endo preference for the vinyl ether together with an intrinsic facial bias in the auxiliary. © 1990.

引用

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页码：4857 / 4876

页数：20

相关论文

共 88 条

[1] 2-PHENYLSULFONYL 1,3-DIENES IN ASYMMETRIC DIELS-ALDER REACTIONS WITH CHIRAL ENAMINES AND ENOL ETHERS [J].

BACKVALL, JE ;

RISE, F .

TETRAHEDRON LETTERS, 1989, 30 (39) :5347-5348

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

BARRETT, AGM ;

GRABOSKI, GG .

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

[3] OXONIUM ION ELECTROPHILES - SYNTHESIS OF THE HYPOTENSIVE OUDENONE [J].

BATES, HA ;

FARINA, J .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3843-3845

[4] MILD LEWIS ACID CATALYSIS - EU(FOD)3-MEDIATED HETERO-DIELS-ALDER REACTION [J].

BEDNARSKI, M ;

DANISHEFSKY, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) :3716-3717

[5] CHIRAL INDUCTION IN THE CYCLOCONDENSATION OF ALDEHYDES WITH SILOXYDIENES [J].

BEDNARSKI, M ;

MARING, C ;

DANISHEFSKY, S .

TETRAHEDRON LETTERS, 1983, 24 (33) :3451-3454

[6] INTERACTIVITY OF CHIRAL CATALYSTS AND CHIRAL AUXILIARIES IN THE CYCLOADDITION OF ACTIVATED DIENES WITH ALDEHYDES - A SYNTHESIS OF L-GLUCOSE [J].

BEDNARSKI, M ;

DANISHEFSKY, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7060-7067

[7] SYNTHESIS OF ISOPINOCAMPHEYLHALOGEN BORANES AND THEIR USE AS CHIRAL CATALYSTS FOR ASYMMETRICAL DIELS-ALDER REACTIONS [J].

BIR, G ;

KAUFMANN, D .

TETRAHEDRON LETTERS, 1987, 28 (07) :777-780

[8] ASYMMETRIC MICHAEL-ADDITIONS - PRACTICALLY COMPLETELY DIASTEREOSELECTIVE AND ENANTIOSELECTIVE ALKYLATIONS OF THE ENAMINE FROM CYCLOHEXANONE AND PROLINYL METHYL-ETHER BY OMEGA-NITROSTYRENES TO GIVE U- 2-(1'-ARYL-2'-NITROETHYL)CYCLOHEXANONES [J].

BLARER, SJ ;

SCHWEIZER, WB ;

SEEBACH, D .

HELVETICA CHIMICA ACTA, 1982, 65 (05) :1637-1654

[9] ASYMMETRIC MICHAEL ADDITIONS - REGIO-SELECTIVE, DIASTEREO-SELECTIVE, AND ENANTIOSELECTIVE ALKYLATIONS OF THE ENAMINES FROM BETA-TETRALONES AND (S)-2-(METHOXYMETHYL)PYRROLIDINE (PROLINOL METHYL-ETHER) BY OMEGA-NITROSTYRENES [J].

BLARER, SJ ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (09) :3086-3096

[10] ASYMMETRIC MICHAEL ADDITIONS - STEREOSELECTIVE ALKYLATIONS OF THE (R)-ENAMINE AND (S)-ENAMINE FROM CYCLOHEXANONE AND 2-(METHOXYMETHYL)PYRROLIDINE BY METHYL ALPHA-(METHOXYCARBONYL)CINNAMATES [J].

BLARER, SJ ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (06) :2250-2260

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