Enantioselective Cu-catalyzed 1,4-addition of Me(3)Al to a 4,4-disubstituted cyclohexa-2,5-dienone: Novel effect of TrialkylsilylOTf on enantioselectivity

被引：43

作者：

Takemoto, Y ^{[1
]}

Kuraoka, S ^{[1
]}

Hamaue, N ^{[1
]}

Iwata, C ^{[1
]}

机构：

[1] TANABE SEIYAKU CO LTD,PROD TECHNOL DIV,YODOGAWA KU,OSAKA 532,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 04期

关键词：

D O I：

10.1016/0957-4166(96)00100-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric Cu-catalyzed conjugate addition of Me(3)Al to cyclohexa-2,5-dienone in the presence of 20 mol% of chiral 2-aryloxazolines and 120 mol% of TBDMSOTf gave the corresponding addition product in good yield with enantiomeric purities of up to 68% ee under mild conditions. Without TBDMSOTf, the ee was dramatically decreased, even in the presence of chiral 2-aryloxazolines. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：993 / 996

页数：4

共 31 条

[1] CHIRAL PHOSPHORUS LIGANDS FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS
ALEXAKIS, A
FRUTOS, J
MANGENEY, P
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2427 - 2430
[2] PREPARATION OF NOVEL SULFUR AND PHOSPHORUS-CONTAINING OXAZOLINES AS LIGANDS FOR ASYMMETRIC CATALYSIS
ALLEN, JV
DAWSON, GJ
FROST, CG
WILLIAMS, JMJ
COOTE, SJ
[J]. TETRAHEDRON, 1994, 50 (03) : 799 - 808
[3] PALLADIUM-CATALYZED ASYMMETRIC ALLYLIC SUBSTITUTION - A LIGAND DESIGN INCORPORATING STERIC AND ELECTRONIC EFFECTS
ALLEN, JV
COOTE, SJ
DAWSON, GJ
FROST, CG
MARTIN, CJ
WILLIAMS, JMJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (15): : 2065 - 2072
[4] ALPHA-AMINO ESTER DERIVATIVES AS NUCLEOPHILES IN STEREOSELECTIVE PALLADIUM-CATALYZED ALLYLIC SUBSTITUTION-REACTIONS
BALDWIN, IC
WILLIAMS, JMJ
BECKETT, RP
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (07) : 1515 - 1518
[5] BALM C, 1991, CHEM BER, V124, P1173
[6] EFFECT OF TMSCL ON THE CONJUGATE ADDITION OF ORGANOCUPRATES TO ALPHA-ENONES - A NEW MECHANISM
BERTZ, SH
MIAO, GB
ROSSITER, BE
SNYDER, JP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) : 11023 - 11024
[7] CLARK DA, 1994, TETRAHEDRON, V50, P11391
[8] PREPARATION AND PROPERTIES OF A SERIES OF ALKYL-4,4-DIMETHYLCYCLOHEXA 2,5-DIENONES, AND RELATED CYCLOHEXENONES AND CYCLOHEXANONES
COOK, KL
WARING, AJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (05): : 529 - 537
[9] SULFIDES TETHERED TO OXAZOLINES - LIGANDS FOR ENANTIOSELECTIVE CATALYSIS
DAWSON, GJ
FROST, CG
MARTIN, CJ
WILLIAMS, JMJ
[J]. TETRAHEDRON LETTERS, 1993, 34 (48) : 7793 - 7796
[10] PREPARATION OF CHIRAL BISOXAZOLINES - OBSERVATIONS ON THE EFFECT OF SUBSTITUENTS
DENMARK, SE
NAKAJIMA, N
NICAISE, OJC
FAUCHER, AM
EDWARDS, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) : 4884 - 4892

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