Synthesis of optically active bridged cyclopropane derivatives

Authors
Glaser, R Neumann, M Ott, F Peters, EM Peters, K von Schnering, HG Tochtermann, W
Citation
R. Glaser et al., Synthesis of optically active bridged cyclopropane derivatives, TETRAHEDRON, 57(18), 2001, pp. 3927-3937
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
18
Year of publication
2001
Pages
3927 - 3937
Database
ISI
SICI code
0040-4020(20010430)57:18<3927:SOOABC>2.0.ZU;2-1
Abstract
Treatment of the cyclobutene 3 with sodium methoxide leads to the cycloprop ane esters 4 and 5. Experiments with deuterated compounds supply informatio n about the course of this reaction. The optically active epoxyoxepine (+)- 2a is the starting material for the synthesis of (+)-3, (-)-4 and (+)-5. Th e syntheses of the functionalized cyclopropanes (+)-10a, (-)-10b and (+)-12 are also described. (C) 2001 Elsevier Science Ltd. All rights reserved.