Catalytic enantioselective Michael additions to unsaturated ester derivatives using chiral copper(II) Lewis acid complexes

被引：96

作者：

Evans, DA ^{[1
]}

Willis, MC ^{[1
]}

Johnston, JN ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 06期

关键词：

D O I：

10.1021/ol9901570

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Chiral Cu(II) bisoxazoline (box) Lewis acids have been developed as catalysts of the Michael addition of enolsilanes to unsaturated ester derivatives, While enantioselection is stereoregular, the sense of diastereoselection is directly related to thioester enolsilane geometry: (E) enolsilanes give anti adducts and (Z) enolsilanes afford syn adducts, The size of the enolsilane alkylthio substituent directly impacts the magnitude of diastereoselection.

引用

页码：865 / 868

页数：4

共 28 条

[1] [Anonymous], 1991, Comprehensive Organic Synthesis
[2] Enantioselective Mukaiyama-Michael reactions of 2-carbomethoxy cyclopentenone catalyzed by chiral bis(oxazoline)-Cu(II) complexes
Bernardi, A
Colombo, G
Scolastico, C
[J]. TETRAHEDRON LETTERS, 1996, 37 (49) : 8921 - 8924
[3] Enantioselective conjugate additions of silylketene acetals to 2-carboxycyclopentenones promoted by chiral Ti complexes
Bernardi, A
Karamfilova, K
Sanguinetti, S
Scolastico, C
[J]. TETRAHEDRON, 1997, 53 (38) : 13009 - 13026
[4] Design and synthesis of the cartilage protective agent (CPA, Ro32-3555)
Broadhurst, MJ
Brown, PA
Lawton, G
Ballantyne, N
Borkakoti, N
Bottomley, KMK
Cooper, MI
Eatherton, AJ
Kilford, IR
Malsher, PJ
Nixon, JS
Lewis, EJ
Sutton, BM
Johnson, WH
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (17) : 2299 - 2302
[5] CATALYTIC, ENANTIOSELECTIVE ALDOL ADDITIONS WITH METHYL AND ETHYL-ACETATE O-SILYL ENOLATES - A CHIRAL TRIDENTATE CHELATE AS A LIGAND FOR TITANIUM(IV)
CARREIRA, EM
SINGER, RA
LEE, WS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) : 8837 - 8838
[6] Davidson AH, 1997, CHEM IND-LONDON, P258
[7] C2-symmetric Cu(II) complexes as chiral Lewis acids.: Catalytic enantioselective Michael addition of silylketene acetals to alkylidene malonates
Evans, DA
Rovis, T
Kozlowski, MC
Tedrow, JS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (09) : 1994 - 1995
[8] An improved procedure for the preparation of 2,2-bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane [(S,S)-tert-butylbis(oxazoline)] and derived copper(II) complexes
Evans, DA
Peterson, GS
Johnson, JS
Barnes, DM
Campos, KR
Woerpel, KA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (13) : 4541 - 4544
[9] C-2-SYMMETRIC CATIONIC COPPER(II) COMPLEXES AS CHIRAL LEWIS-ACIDS - COUNTERION EFFECTS IN THE ENANTIOSELECTIVE DIELS-ALDER REACTION
EVANS, DA
MURRY, JA
VONMATT, P
NORCROSS, RD
MILLER, SJ
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07): : 798 - 800
[10] BIS(OXAZOLINE)COPPER(II) COMPLEXES AS CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE DIELS-ALDER REACTION
EVANS, DA
MILLER, SJ
LECTKA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) : 6460 - 6461

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