trans-1,3-Dithiane-1,3-dioxide, a new chiral acyl anion equivalent for the preparation of masked activated acids: application to the synthesis of α-hydroxy acid derivatives

Abstract

trans-I ,3-Dithiane-l,3-dioxide reacts with high diastereoselectivity with aromatic aldehydes and the 1,3-dithiane-I ,3dioxide moiety can be easily converted to a thiolester without racemisation by carrying out a Pummerer reaction; the thiolester is a group that can be readily transformed into acids, esters, amides, ketones and aldehydes.

The Chemistry of C2‐Symmetric Bis(sulfoxides): A New Approach in Asymmetric Synthesis

“…[80,81] Based on an initial Pummerer reaction, several enantioenriched derivatives of α-hydroxy acids were readily obtained, as illustrated in Scheme 16. [80,81] Based on an initial Pummerer reaction, several enantioenriched derivatives of α-hydroxy acids were readily obtained, as illustrated in Scheme 16.…”

Asymmetric oxidation of substituted dithianes and dithiolanes by engineered yeast and E.coli expressing cyclohexanone monooxygenase

“…Chiral sulfoxides derived from 1,3-dithianes and dithiolanes are valuable asymmetric building blocks and chiral auxiliaries for a wide range of organic reactions, 22,23 but the preparation of these compounds in optically pure form is difficult. 24 Bio-oxidations of simple 1,3-dithianes and dithiolanes 5,8,12,16,17 demonstrated that CHMO from Acinetobacter is an important catalyst for this reactions, and our earlier studies, 12 as well as the results presented in this paper, demonstrate that several such compounds, including very useful and highly interesting 2a and 3a, can be prepared using the recombinant organisms overexpressing CHMO.…”

The Chemistry of C2-Symmetric Bis(sulfoxides): A New Approach in Asymmetric Synthesis

“…Taking advantage of the high diastereoselectivity observed with aromatic aldehydes in all these reactions, Aggarwal et al used ( R , R )‐(+)‐1,3‐dithiane 1,3‐dioxide ( 26 ) as starting material in view of preparing enantiopure materials 80,81…”