Enantioselective synthesis of spiropentanes from hydroxymethylallenes

Authors
Charette, AB Jolicoeur, E Bydlinski, GAS
Citation
Ab. Charette et al., Enantioselective synthesis of spiropentanes from hydroxymethylallenes, ORG LETT, 3(21), 2001, pp. 3293-3295
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
21
Year of publication
2001
Pages
3293 - 3295
Database
ISI
SICI code
1523-7060(20011018)3:21<3293:ESOSFH>2.0.ZU;2-Q
Abstract
[GRAPHICS] Hydroxymethylallenes are efficiently converted to the corresponding spirope ntanes in high yields and enantiomeric ratios upon treatment with Zn(CH(2)l )(2) and dioxaborolane ligand 1. The reaction also proceeds with complete d iastereocontrol, The application of this methodology to the synthesis of sp iropentaneacetic acid is also presented.