Highly Enantioselective Synthesis of γ-Hydroxy-α,β-acetylenic Esters by Asymmetric Alkyne Addition to Aldehydes

Alkynoates are added to aromatic and α,β‐unsaturated aldehydes in the synthesis of the title compounds in optically active form. This highly enantioselective and useful method is carried out under mild reaction conditions and employs the readily available chiral 1,1′‐bi‐2‐naphthol (binol) ligand and...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2005-12, Vol.45 (1), p.122-125
Main Authors: Gao, Ge, Wang, Qin, Yu, Xiao-Qi, Xie, Ru-Gang, Pu, Lin
Format: Article
Language:English
Subjects:
Acetylation
aldehydes
Aldehydes - chemistry
alkynes
Alkynes - chemistry
asymmetric synthesis
binol ligands
esters
Esters - chemical synthesis
Esters - chemistry
Hydroxylation
Molecular Structure
Stereoisomerism
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Summary:Alkynoates are added to aromatic and α,β‐unsaturated aldehydes in the synthesis of the title compounds in optically active form. This highly enantioselective and useful method is carried out under mild reaction conditions and employs the readily available chiral 1,1′‐bi‐2‐naphthol (binol) ligand and the metal reagents Et2Zn and [Ti(OiPr)4] (see scheme; HMPA=hexamethylphosphoramide).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200500469