Synthesis, resolution, and absolute stereochemistry of (1R,2S)-(+)-cis-1-methoxycarbonyl-2-methylcyclobutane

Authors
Baldwin, JE Burrell, RC
Citation
Je. Baldwin et Rc. Burrell, Synthesis, resolution, and absolute stereochemistry of (1R,2S)-(+)-cis-1-methoxycarbonyl-2-methylcyclobutane, J ORG CHEM, 65(21), 2000, pp. 7139-7144
Citations number
38
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
21
Year of publication
2000
Pages
7139 - 7144
Database
ISI
SICI code
0022-3263(20001020)65:21<7139:SRAASO>2.0.ZU;2-Y
Abstract
Racemic cis-1-methoxycarbonyl-2-methylcyclobutane uncontaminated with the t rans isomer was prepared efficiently in five steps; the corresponding amide s from (R)-(-)-phenylglycinol were separated. An X-ray crystallographic str ucture determination of the amide from (+)-cis-1-methoxycarbonyl-2-methylcy clobutane showed that it was of (1R,2S) absolute stereochemistry, a revisio n of configurational assignment.