CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF CHIRAL ALKOXYDIMETHYLCUPRATE TO (E)-CYCLOPENTADEC-2-ENONE

被引：17

作者：

TANAKA, K ^{[1
]}

MATSUI, J ^{[1
]}

SUZUKI, H ^{[1
]}

WATANABE, A ^{[1
]}

机构：

[1] NIPPON MIN CO LTD,BIOSCI RES LABS,TODA,SAITAMA 335,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 10期

关键词：

D O I：

10.1039/p19920001193

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric 1,4-addition of methyllithium to (E)-cyclopentadec-2-enone was promoted by the chiral cuprate catalyst prepared from (1R,2R,3S,4S)-3-[(1 -methylpyrrol-2-yl)methylamino]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol and copper(I) iodide to give (R)-(-)-muscone in 76% chemical yield and 96% enantiomeric excess.

引用

页码：1193 / 1194

页数：2

共 17 条

[1] ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL CUPRATE COMPLEXES
AHN, KH
KLASSEN, RB
LIPPARD, SJ
[J]. ORGANOMETALLICS, 1990, 9 (12) : 3178 - 3181
[2] NEW CHIRAL LIGAND FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO ENONES
ALEXAKIS, A
MUTTI, S
NORMANT, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) : 6332 - 6334
[3] ASYMMETRIC INDUCTION WITH AMIDOCUPRATES
BERTZ, SH
DABBAGH, G
SUNDARARAJAN, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) : 4953 - 4959
[4] ENANTIOSELECTIVE CONJUGATE ADDITION OF RATIONALLY DESIGNED CHIRAL CUPRATE REAGENTS TO 2-CYCLOALKENONES
COREY, EJ
NAEF, R
HANNON, FJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) : 7114 - 7116
[5] ASYMMETRIC INDUCTION IN THE CONJUGATE ADDITION-REACTIONS OF CHIRAL ORGANO(HETERO)CUPRATES
DIETER, RK
TOKLES, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) : 2040 - 2046
[6] CHEMISTRY OF CARBANIONS .12. ROLE OF COPPER INCONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS
HOUSE, HO
RESPESS, WL
WHITESID.GM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (10) : 3128 - &
[7] REACTIONS INVOLVING ELECTRON-TRANSFER .12. EFFECTS OF SOLVENT AND SUBSTITUENTS UPON ABILITY OF LITHIUM DIORGANOCUPRATES TO ADD TO ENONES
HOUSE, HO
WILKINS, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) : 2443 - 2454
[8] ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL ZINC(II) COMPLEXES
JANSEN, JFGA
FERINGA, BL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) : 4168 - 4175
[9] ENANTIOSELECTIVE 1,4-ADDITIONS OF ORGANOMETALLIC COMPOUNDS TO CONJUGATED SYSTEMS IN THE CHIRAL MEDIUM DDB
LANGER, W
SEEBACH, D
[J]. HELVETICA CHIMICA ACTA, 1979, 62 (06) : 1710 - 1722
[10] ENANTIOSELECTIVE CONJUGATE ADDITION WITH CHIRAL AMIDOCUPRATES
ROSSITER, BE
EGUCHI, M
[J]. TETRAHEDRON LETTERS, 1990, 31 (07) : 965 - 968

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