Enantioselective Alkynylations of Aromatic and Aliphatic Aldehydes Catalyzed by Terpene Derived Chiral Amino Alcohols.

Abstract Enantioselective alkynyl zinc additions to aromatic and aliphatic aldehydes have been studied using terpene derived chiral amino alcohol ligands. The limonene derived amino alcohol (1 R ,2 R ,5 S )-2-methyl-5-(1-methylethenyl)-2-(1-pyrrolidinyl)cyclohexanol gave the most promising results. Chiral propargylic alcohols were obtained in good yields and moderate enantioselectivities (up to 60%).