Asymmetric iodocyclization of γ-hydroxyalkenes

被引:26
作者
Kang, SH [1 ]
Park, CM [1 ]
Lee, SB [1 ]
Kim, M [1 ]
机构
[1] Korea Adv Inst Sci & Technol, Sch Mol Sci BK21, Dept Chem, Ctr Mol Design & Synth, Taejon 305701, South Korea
关键词
reagent-controlled; iodocyclization; gamma-hydroxyalkenes; (R)-Binol-Ti(IV) complex; N-iodosuccinimide;
D O I
10.1055/s-2004-825593
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantioselective intramolecular iodoetherification of disubstituted gamma-hydroxyalkenes has been intended using NIS in the presence of 0.2 equivalents of (R)-Binol-Ti(IV) complex to procure the corresponding tetrahydrofurans in up to 65% ee.
引用
收藏
页码:1279 / 1281
页数:3
相关论文
共 24 条
[1]   Asymmetric electrophilic methoxyselenenylations and cyclizations with 3-camphorseleno derivatives [J].
Back, TG ;
Dyck, BP ;
Nan, SQ .
TETRAHEDRON, 1999, 55 (11) :3191-3208
[2]  
CARLSON RM, 1971, TETRAHEDRON LETT, P3661
[3]   HOST-GUEST COMPLEXATION .8. MACROCYCLIC POLYETHERS SHAPED BY 2 RIGID SUBSTITUTED DINAPHTHYL OR DITETRALYL UNITS [J].
CRAM, DJ ;
HELGESON, RC ;
PEACOCK, SC ;
KAPLAN, LJ ;
DOMEIER, LA ;
MOREAU, P ;
KOGA, K ;
MAYER, JM ;
CHAO, Y ;
SIEGEL, MG ;
HOFFMAN, DH ;
SOGAH, GDY .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :1930-1946
[4]  
FUJI K, 1990, TETRAHEDRON LETT, V31, P3175
[5]   ASYMMETRIC OXYSELENENYLATION OF OLEFINS USING OPTICALLY-ACTIVE SELENOBINAPHTHYLS AND D-MENTHOL AS A NUCLEOPHILE [J].
FUJITA, K ;
IWAOKA, M ;
TOMODA, S .
CHEMISTRY LETTERS, 1992, (07) :1123-1124
[6]  
FURTH M, 1987, J AM CHEM SOC, V109, P6844
[7]   The first reagent-controlled asymmetric halolactonizations. Dihydroquinidine-halogen complexes as chiral sources of positive halogen ion [J].
Grossman, RB ;
Trupp, RJ .
CANADIAN JOURNAL OF CHEMISTRY, 1998, 76 (09) :1233-1237
[8]   ASYMMETRIC INDUCTION IN CYCLIZATION OF O-ALLYLPHENOL WITH CHIRAL MERCURY(II) CARBOXYLATES - EFFECT OF DIMETHYL SULFOXIDE [J].
GRUNDON, MF ;
STEWART, D ;
WATTS, WE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (16) :573-574
[9]   Reagent-controlled stereoselective iodolactonizations [J].
Haas, J ;
Piguel, S ;
Wirth, T .
ORGANIC LETTERS, 2002, 4 (02) :297-300
[10]  
HARDING KE, 1991, COMPREHENSIVE ORGANI, V4, P463