Catalytic Asymmetric Synthesis of Macrocyclic (E)-Allylic Alcohols from ω-Alkynals via Intramolecular 1-Alkenylzinc/Aldehyde Additions
- 20 June 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (14) , 4766-4770
- https://doi.org/10.1021/jo000463n
Abstract
The ω-alkynals yielded macrocyclic (S)-allylic alcohols in a one-pot reaction sequence involving alkyne monohydroboration, boron to zinc transmetalation, and ((+)-DAIB)-catalyzed enantioselective intramolecular ring closure to the aldehyde function. A general study of this macrocyclization methodology is presented with respect to ligand type, size, and nature of the formed rings.Keywords
This publication has 19 references indexed in Scilit:
- Total synthesis of the macrolide (+)-aspicilin by an asymmetrically catalyzed macrocyclization of an ω-Alkynal esterTetrahedron Letters, 1995
- Synthesis of (R)-(-)-muscone by an asymmetrically catalyzed macrocyclization of an .omega.-alkynalJournal of the American Chemical Society, 1993
- Enantioselective addition of organozinc reagents to aldehydesChemical Reviews, 1992
- Catalytic asymmetric synthesis of Secondary (E)‐allyl alcohols from acetylenes and aldehydes via (1‐alkenyl)zinc intermediates. Preliminary CommunicationHelvetica Chimica Acta, 1992
- Enantioselective addition of (Z)- and (E)-alkenylzinc bromides to aldehydes: asymmetric synthesis of sec-allylalcoholsTetrahedron Letters, 1991
- Enantioselective Addition of Organometallic Reagents to Carbonyl Compounds: Chirality Transfer, Multiplication, and AmplificationAngewandte Chemie International Edition in English, 1991
- Selective Cleavage of Dimethylhydrazones to the Carbonyl Compounds Using Silica Gel and its Application in the Synthesis of (Z)-9-Tetradecenyl AcetateSynthesis, 1989
- Enantioselective synthesis of sec-allylalcohols by catalytic asymmetric addition of divinylzinc to aldehydes.Tetrahedron Letters, 1988
- Alkyne isomerization reagents: mixed alkali metal amidesCanadian Journal of Chemistry, 1984
- Activated Dimethyl Sulfoxide: Useful Reagents for SynthesisSynthesis, 1981