Catalytic asymmetric synthesis of macrocyclic (E)-allylic alcohols from omega-alkynals via intramolecular 1-alkenylzinc/aldehyde additions

Authors
Oppolzer, W Radinov, RN El-Sayed, E
Citation
W. Oppolzer et al., Catalytic asymmetric synthesis of macrocyclic (E)-allylic alcohols from omega-alkynals via intramolecular 1-alkenylzinc/aldehyde additions, J ORG CHEM, 66(14), 2001, pp. 4766-4770
Citations number
24
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
14
Year of publication
2001
Pages
4766 - 4770
Database
ISI
SICI code
0022-3263(20010713)66:14<4766:CASOM(>2.0.ZU;2-5
Abstract
The omega -alkynals yielded macrocyclic (S)-allylic alcohols in a one-pot r eaction sequence involving alkyne monohydroboration, boron to zinc transmet alation, and ((+)-DAIB)-catalyzed enantioselective intramolecular ring clos ure to the aldehyde function. A general study of this macrocyclization meth odology is presented with respect to ligand type, size, and nature of the f ormed rings.