Citation
Pv. Ramachandran et al., A facile synthesis of chiral omega-allyl- and omega-n-propyllactones via asymmetric allylboration of formyl esters with B-allyldiisopinocampheylborane, TETRAHEDR-A, 10(1), 1999, pp. 11-15
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166
→ ACNP
Volume
10
Issue
1
Year of publication
1999
Pages
11 - 15
Database
ISI
SICI code
0957-4166(19990115)10:1<11:AFSOCO>2.0.ZU;2-U
Abstract
Asymmetric allylboration of aldehydes containing an adjacent ester group wi
th B-allyldiisopinocampheylborane, followed by hydrolysis and cyclization,
provides the corresponding allyl substituted lactones in high yields and gr
eater than or equal to 92% enantiomeric excess. Hydrogenation of these lact
ones provides the corresponding propyl substituted lactones without any los
s of optical purity. (C) 1999 Elsevier Science Ltd. All rights reserved.