960054-30-2Relevant academic research and scientific papers
Development of Zn-prophenol-catalyzed asymmetric alkyne addition: Synthesis of chiral propargylic alcohols
Trost, Barry M.,Bartlett, Mark J.,Weiss, Andrew H.,Vonwangelin, Axel Jacobi,Chan, Vincent S.
, p. 16498 - 16509 (2013/02/23)
The development of a general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported. The commercially available ProPhenol ligand (1) has facilitated the addition of a wide range of zinc alkynylides to aryl, aliphatic, and α,β-unsaturated aldehydes in high yield and enantioselectivity. New insights into the mechanism of this reaction have resulted in a significant reduction in reagent stoichiometry, enabling the use of precious alkynes and avoiding the use of excess dimethylzinc. The enantioenriched propargylic alcohols from this reaction serve as versatile synthetic intermediates and have enabled efficient syntheses of several complex natural products. A precious few: A general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported (see scheme). New insights into the mechanism of this reaction have resulted in a significant reduction in reagent stoichiometry, enabling the use of precious alkynes and avoiding the use of excess dimethylzinc. This methodology has enabled the efficient synthesis of several complex natural products.
An alkyne strategy for the asymmetric synthesis of natural products: Application to (+)-spirolaxine methyl ether
Trost, Barry M.,Weiss, Andrew H.
, p. 7664 - 7666 (2008/09/18)
(Chemical Equation Presented) Alkyne of magic: An efficient synthesis of (+)-spirolaxine methyl ether (1) was accomplished by using alkynes as versatile synthetic building blocks. Highlights include two ProPhenol-catalyzed asymmetric alkynylations and a P
