ENANTIOSPECIFIC PREPARATION OF GEM-DIMETHYLCYCLOPROPANE FUSED CYCLOHEPTANES VIA VALENCE TAUTOMERIZATION OF 3,4-HOMOTROPILIDENE UNDER THERMODYNAMIC AND KINETIC CONTROL

Authors
SUGIMURA T FUTAGAWA T KATAGIRI T NISHIYAMA N TAI A
Citation
T. Sugimura et al., ENANTIOSPECIFIC PREPARATION OF GEM-DIMETHYLCYCLOPROPANE FUSED CYCLOHEPTANES VIA VALENCE TAUTOMERIZATION OF 3,4-HOMOTROPILIDENE UNDER THERMODYNAMIC AND KINETIC CONTROL, Tetrahedron letters, 37(40), 1996, pp. 7303-7306
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
40
Year of publication
1996
Pages
7303 - 7306
Database
ISI
SICI code
0040-4039(1996)37:40<7303:EPOGFC>2.0.ZU;2-B
Abstract
3,4-Homotropilidene derivatives were obtained as a stable compound by regioselective dichlorocarbene addition to 4-alkoxy-8,8-dimethyIcycloh eptatrienes. Substitution of chlorine atomes to hydrogens in them by r eduction with sodium affords rearranged products. By using stereospeci ficity of the rearrangement, the corresponding optically active produc ts were also prepared. Copyright (C) 1996 Elsevier Science Ltd