ASYMMETRIC ADDITION OF ACETYLIDE TO ALIPHATIC ALDEHYDES—PREPARATION OF OPTICALLY ACTIVE 5-OCTYL-2(5H)-FURANONE—
- 5 March 1980
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 9 (3) , 255-256
- https://doi.org/10.1246/cl.1980.255
Abstract
Various optically active acetylenic alcohols (40-80%e.e.) were obtained by enantioface-differentiating addition of lithium trimethylsilylacetylide to aliphatic aldehydes utilizing (2S, 2′S)-2-hydroxymethyl-1-[(1-methylpyrrolidin-2-yl)methyl]pyrrolidine as a chiral ligand. Optically active (R)-1-trimethylsilyl-l-undecyn-3-ol (80%e.e.) was transformed into optically active 5-octyl-2(5H)-furanone in good yield.Keywords
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