(S)-(-)-2-TERT-BUTYL-3-METHYLENE-OXIRANE - SYNTHESIS AND HYDROBORATION OF A CHIRAL ALLENE OXIDE

Authors
KONOIKE T HAYASHI T ARAKI Y
Citation
T. Konoike et al., (S)-(-)-2-TERT-BUTYL-3-METHYLENE-OXIRANE - SYNTHESIS AND HYDROBORATION OF A CHIRAL ALLENE OXIDE, Tetrahedron : asymmetry, 5(8), 1994, pp. 1559-1566
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
8
Year of publication
1994
Pages
1559 - 1566
Database
ISI
SICI code
0957-4166(1994)5:8<1559:(-SAH>2.0.ZU;2-H
Abstract
The chiral allene oxide, (S)-(-)-2-tert-butyl-3-methylene-oxirane 12 ( (S)-(-)-1-tert-butylallene oxide) was prepared in a moderate yield and in high enantiomeric excess by a three-step conversion starting from 4,4-dimethyl-2-pentyn-1-ol 6. The procedure was comprised of hydrostan nylation, Sharpless epoxidation and deoxystannylation. The chiral alle ne oxide 12 has moderate stability for identification and characteriza tion and undergoes hydroboration to afford a chiral diol, (R)4,4-dimet hylpentane-1,3-diol 15.