STEREOCHEMICAL INVESTIGATIONS OF SAMARIUM(II) IODIDE-PROMOTED 5-EXO AND 6-EXO KETYL-OLEFIN RADICAL CYCLIZATION REACTIONS

被引：98

作者：

MOLANDER, GA

MCKIE, JA

机构：

[1] Department of Chemistry, Biochemistry, University of Colorado, Boulder

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 04期

关键词：

D O I：

10.1021/jo00109a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Samarium(II) iodide (SmI2)-promoted ketyl cyclizations of several substituted, unsaturated ketones, providing various cyclopentyl and cyclohexyl systems, have been investigated. The resulting experiments provide stereochemical insight into these reactions and in addition outline the synthetic potential of these 5-exe and 6-exo radical cyclization processes.

引用

页码：872 / 882

页数：11

共 41 条

[1] STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUND ADDITION TO KETONES
ASHBY, EC
LAEMMLE, JT
[J]. CHEMICAL REVIEWS, 1975, 75 (04) : 521 - 546
[2] SYNTHESES OF ISOCARBACYCLIN BY HIGHLY REGIOSELECTIVE ALKYLATION OF ALLYLIC ALCOHOLS
BANNAI, K
TANAKA, T
OKAMURA, N
HAZATO, A
SUGIURA, S
MANABE, K
TOMIMORI, K
KATO, Y
KUROZUMI, S
NOYORI, R
[J]. TETRAHEDRON, 1990, 46 (19) : 6689 - 6704
[3] BECKWITH ALJ, 1992, TETRAHEDRON, V48, P4641
[4] REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY
BECKWITH, ALJ
SCHIESSER, CH
[J]. TETRAHEDRON, 1985, 41 (19) : 3925 - 3941
[5] REGIO-SELECTIVITY AND STEREO-SELECTIVITY IN RADICAL REACTIONS
BECKWITH, ALJ
[J]. TETRAHEDRON, 1981, 37 (18) : 3073 - 3100
[6] SYNTHESIS OF BICYCLIC CYCLOPENTANOLS BY PHOTOREDUCTIVE CYCLIZATION OF DELTA,EPSILON-UNSATURATED KETONES
BELOTTI, D
COSSY, J
PETE, JP
PORTELLA, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (22) : 4196 - 4200
[7] THE DESIGN AND APPLICATION OF FREE-RADICAL CHAIN REACTIONS IN ORGANIC-SYNTHESIS .1.
CURRAN, DP
[J]. SYNTHESIS-STUTTGART, 1988, (06): : 417 - 439
[8] PYRIDINE-INDUCED SOLVENT SHIFTS IN NUCLEAR MAGNETIC RESONANCE SPECTRA OF HYDROXYLIC COMPOUNDS
DEMARCO, PV
FARKAS, E
DODDRELL, D
MYLARI, BL
WENKERT, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) : 5480 - &
[9] EAKIN M, 1965, J CHEM SOC CHEM COMM, P206
[10] SAMARIUM(II) IODIDE MEDIATED TRANSFORMATION OF CARBOHYDRATES TO CARBOCYCLES
ENHOLM, EJ
TRIVELLAS, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (16) : 6463 - 6465

← 1 2 3 4 5 →