Abstract
Catalytic asymmetric S-H insertion of carbenoids generated from aryldiazoacetates has been investigated with a number of chiral Rh(II) and Cu(I) catalysts. 12 % - 23 % ee enantioselectivity were achieved with chiral Rh(II) catalysts.
Highlights
Active α–mercapto carboxylic acid derivatives are ubiquitous structural subunits in numerous biologically active natural and unnatural compounds
The phenyldiazoacetates was employed as the diazo substrate to optimize the reaction conditions
A wide range of chiral catalysts was selected for study (Scheme 3). These chiral catalysts have been demonstrated to be highly effective in asymmetric reaction of carbenoids, such as C-H insertion and cyclopropanation.[7]
Summary
Active α–mercapto carboxylic acid derivatives are ubiquitous structural subunits in numerous biologically active natural and unnatural compounds. Doyle reported the S-H insertion reaction of 3-diazobutan-2-one with thiophenol in the presence of chiral Cu(I) and Rh(II) catalysts.
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