22956-19-0Relevant academic research and scientific papers
N-Heterocyclic carbene-catalyzed sulfa-Michael addition of enals
Cong, Zi-Song,Li, Yang-Guo,Du, Guang-Fen,Gu, Cheng-Zhi,Dai, Bin,He, Lin
, p. 13129 - 13132 (2017/12/26)
An efficient N-heterocyclic carbene (NHC) catalyzed sulfa-Michael addition (SMA) between enals and thiols has been developed. Under the catalysis of 10 mol% stable free carbene IPr and with 20 mol% hexafluoroisopropanol (HFIP) as an additive, enals react with a variety of thiols to afford the SMA adducts in 54-98% yields. In this process, the free carbene preferentially interacts with thiols through hydrogen-bonding and no NHC-catalyzed extended Umpolung transformations were observed.
Selectivity reversal during thia-Michael additions using tetrabutylammonium hydroxide: Operationally simple and extremely high turnover
Nicponski, Daniel R.,Marchi, Jennifer M.
supporting information, p. 1725 - 1730 (2014/07/08)
The use of tetrabutylammonium hydroxide as a novel and exceedingly efficient thia-Michael addition catalyst is herein described. This extremely simple methodology allows for the conjugate addition of a wide variety of mercaptan nucleophiles, and functions remarkably well with a very wide range of both classical and non-classical Michael acceptors. Contradistinctive to current literature reports, the use of this catalyst more efficiently promotes the addition of more basic thiols. This methodology is especially attractive and operationally simple, as it generally proceeds with only 1 mol% catalytic loading and without excess reagent, and the produced products typically require no purification. Georg Thieme Verlag Stuttgart New York.
TMAF-catalyzed conjugate addition of oxazolidinone and thiols
Ménand, Micka?l,Dalla, Vincent
, p. 95 - 98 (2007/10/03)
TMAF (Me4NF) is a useful catalyst for the conjugate addition of oxazolidinone and thiols to a range of Michael acceptors including esters, ketones, nitroolefins and cinnamaldehyde.
Novel heterobimetallic catalysts for asymmetric Michael reactions
Velmathi,Swarnalakshmi,Narasimhan
, p. 113 - 117 (2007/10/03)
The newly developed chiral catalysts 1 and 2 show opposite enantioselectivity in Michael addition reactions of cyclic enones and malonates resulting in the production of both enantiomers of products in good chemical yield and enantiomeric excess. 27
