133576-75-7Relevant articles and documents
Enantioselective Conjugate Addition of Catalytically Generated Zinc Homoenolate
Sekiguchi, Yoshiya,Yoshikai, Naohiko
supporting information, p. 4775 - 4781 (2021/04/07)
We report herein an enantioselective conjugate addition reaction of a zinc homoenolate, catalytically generated via ring opening of a cyclopropanol, to an α,β-unsaturated ketone. The reaction is promoted by a zinc aminoalkoxide catalyst generated from Et2Zn and a chiral β-amino alcohol to afford 1,6-diketones, which undergo, upon heating, intramolecular aldol condensation to furnish highly substituted cyclopentene derivatives with good to high enantioselectivities. The reaction has proved applicable to various 1-substituted cyclopropanols as well as chalcones and related enones. The chiral amino alcohol has proved to enable ligand-accelerated catalysis of the homoenolate generation and its conjugate addition. Positive nonlinear effects and lower reactivity of a racemic catalyst have been observed, which can be attributed to a stable and inactive heterochiral zinc aminoalkoxide dimer.
New chiral catalysts for the highly enantioselective addition of diethylzinc to aldehydes
Jin, Myung-Jong,Ahn, Sum-Jin,Lee, Kyoung-Soo
, p. 8767 - 8770 (2007/10/03)
Optically active amino thioacetate derivatives of (+)-norephedrine were found to act as effective catalysts for enantioselective addition of diethylzinc to aldehydes. This reaction provided optically active secondary alcohols with e.e. of up to >99%.