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

来源：

SYNLETT | 2004年 / 07期

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

页码：1279 / 1281

页数：3

共 24 条

[1] Asymmetric electrophilic methoxyselenenylations and cyclizations with 3-camphorseleno derivatives
Back, TG
Dyck, BP
Nan, SQ
[J]. 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
CRAM, DJ
HELGESON, RC
PEACOCK, SC
KAPLAN, LJ
DOMEIER, LA
MOREAU, P
KOGA, K
MAYER, JM
CHAO, Y
SIEGEL, MG
HOFFMAN, DH
SOGAH, GDY
[J]. 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
FUJITA, K
IWAOKA, M
TOMODA, S
[J]. 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
Grossman, RB
Trupp, RJ
[J]. 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
GRUNDON, MF
STEWART, D
WATTS, WE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (16) : 573 - 574
[9] Reagent-controlled stereoselective iodolactonizations
Haas, J
Piguel, S
Wirth, T
[J]. ORGANIC LETTERS, 2002, 4 (02) : 297 - 300
[10] HARDING KE, 1991, COMPREHENSIVE ORGANI, V4, P463

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