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
收藏
页码:1193 / 1194
页数:2
相关论文
共 17 条
[1]   ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL CUPRATE COMPLEXES [J].
AHN, KH ;
KLASSEN, RB ;
LIPPARD, SJ .
ORGANOMETALLICS, 1990, 9 (12) :3178-3181
[2]   NEW CHIRAL LIGAND FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO ENONES [J].
ALEXAKIS, A ;
MUTTI, S ;
NORMANT, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6332-6334
[3]   ASYMMETRIC INDUCTION WITH AMIDOCUPRATES [J].
BERTZ, SH ;
DABBAGH, G ;
SUNDARARAJAN, G .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4953-4959
[4]   ENANTIOSELECTIVE CONJUGATE ADDITION OF RATIONALLY DESIGNED CHIRAL CUPRATE REAGENTS TO 2-CYCLOALKENONES [J].
COREY, EJ ;
NAEF, R ;
HANNON, FJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7114-7116
[5]   ASYMMETRIC INDUCTION IN THE CONJUGATE ADDITION-REACTIONS OF CHIRAL ORGANO(HETERO)CUPRATES [J].
DIETER, RK ;
TOKLES, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2040-2046
[6]   CHEMISTRY OF CARBANIONS .12. ROLE OF COPPER INCONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS [J].
HOUSE, HO ;
RESPESS, WL ;
WHITESID.GM .
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 [J].
HOUSE, HO ;
WILKINS, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2443-2454
[8]   ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL ZINC(II) COMPLEXES [J].
JANSEN, JFGA ;
FERINGA, BL .
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 [J].
LANGER, W ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1979, 62 (06) :1710-1722
[10]   ENANTIOSELECTIVE CONJUGATE ADDITION WITH CHIRAL AMIDOCUPRATES [J].
ROSSITER, BE ;
EGUCHI, M .
TETRAHEDRON LETTERS, 1990, 31 (07) :965-968