1309206-73-2Relevant academic research and scientific papers
Asymmetric synthesis of chiral β-alkynyl carbonyl and sulfonyl derivatives: Via sequential palladium and copper catalysis
Trost, Barry M.,Masters, James T.,Taft, Benjamin R.,Lumb, Jean-Philip
, p. 6217 - 6231 (2016/08/31)
We present a full account detailing the development of a sequential catalysis strategy for the synthesis of chiral β-alkynyl carbonyl and sulfonyl derivatives. A palladium-catalyzed cross coupling of terminal alkyne donors with acetylenic ester, ketone, a
A new strategy for the synthesis of chiral β-alkynyl esters via sequential palladium and copper catalysis
Trost, Barry M.,Taft, Benjamin R.,Masters, James T.,Lumb, Jean-Philip
, p. 8502 - 8505 (2011/07/08)
A new strategy for the synthesis of chiral β-alkynyl esters which relies on sequential Pd and Cu catalysis is reported. Terminal alkynes bearing aryl, alkyl, and silyl groups can be employed without prior activation yielding a wide range of important chiral building blocks. The reaction sequence utilizes a robust Pd(II)-catalyzed hydroalkynylation of ynoates with terminal alkynes providing geometrically pure ynenoates which are readily reduced by CuH. In contrast to previous reports, where additions to ynenoates proceed with marginal preference for the 1,6-pathway, this conjugate reduction occurs with high 1,4-selectivity yielding β-alkynyl esters with excellent levels of enantioselectivity. Importantly, the method tolerates a wide range of functionality, including allylic carbonates and carbamates, and thus allows for rapid elaboration of the β-alkynyl esters into a variety of chiral, substituted heterocycles.
