A one-pot and efficient preparation of (S)-benzyl 4-hydroxy-2-pentynoate from (S)-3-butyn-2-ol using an unusual lithiation with n-BuLi and a catalytic amount of hexamethyldisilazane

Authors
Lai, GF Colon, C
Citation
Gf. Lai et C. Colon, A one-pot and efficient preparation of (S)-benzyl 4-hydroxy-2-pentynoate from (S)-3-butyn-2-ol using an unusual lithiation with n-BuLi and a catalytic amount of hexamethyldisilazane, SYN COMMUN, 29(17), 1999, pp. 3011-3016
Citations number
5
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
17
Year of publication
1999
Pages
3011 - 3016
Database
ISI
SICI code
0039-7911(1999)29:17<3011:AOAEPO>2.0.ZU;2-O
Abstract
A one-pot, four-step procedure was developed for the efficient preparation of (S)-benzyl 4-hydroxy-2-pentynoate (1) from (S)-3-butyn-2-ol (2), which i nvolved as a key step the unusual lithiation of the silyl ether 5 with n-Bu Li in the presence of a catalylic amount of hexamethyldisilazane (HMDS).