A new asymmetric synthesis of trans-hydroisoquinolones

被引:30
作者
Kamatani, A [1 ]
Overman, LE [1 ]
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
关键词
D O I
10.1021/ol015696v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient enantioselective synthesis of trans-hydroisoquinolones is described. This synthesis capitalizes on the ready availability of enantioenriched 2-substituted cyclohexenols by exploiting the asymmetry of an allylic carbon-oxygen sigma bond to control carbon-carbon bond formation in pinacol-terminated cyclizations of N-acyliminium cations.
引用
收藏
页码:1229 / 1232
页数:4
相关论文
共 25 条
[1]   β-phenylethylamines and the isoquinoline alkaloids [J].
Bentley, KW .
NATURAL PRODUCT REPORTS, 1999, 16 (03) :367-388
[2]   SYNTHESIS OF OPTICALLY-ACTIVE PYRROLIZIDINEDIOLS - (+)-HELIOTRIDINE [J].
CHAMBERLIN, AR ;
CHUNG, JYL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (11) :3653-3656
[3]   Stereocontrolled synthesis of trisubstituted tetrahydropyrans [J].
Cloninger, MJ ;
Overman, LE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :1092-1093
[4]   Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans [J].
Cohen, F ;
MacMillan, DWC ;
Overman, LE ;
Romero, A .
ORGANIC LETTERS, 2001, 3 (08) :1225-1228
[5]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[6]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[7]  
DEKONING H, 1995, METHODS ORGANIC C EB, V21
[8]  
HARAKI N, 2000, ORG LETT, V2, P223
[9]   INTRAMOLECULAR REACTIONS OF ACYCLIC N-ACYLIMINIUM IONS .2. ALLYL SILANES AS NUCLEOPHILES [J].
HIEMSTRA, H ;
FORTGENS, HP ;
SPECKAMP, WN .
TETRAHEDRON LETTERS, 1985, 26 (26) :3155-3158
[10]  
HIEMSTRA H, 1991, COMPREHENSIVE ORGANI, V2