Propane-l-sulfonamide

A one-pot procedure designed for the aziridination of a series of styrene derivatives employs commercially available iodobenzene diacetate [PhI(OAc)2] and sulfonamides (427, RSO2NH2) to generate the nitrene precursors [iV-(arene/methanesulfonyl)imino]phenyliodanes (RS02N=IPh) in situ. The reaction is carried out in the presence of the chiral catalyst CuIMeCNIaClOa-L (436 L = 2,2-bis[2-[(4A)-/-butyl-l,3-oxazolinyl]]propane) to give aziridine 437 (Scheme 113) <2004TL3965>. 

The cross-aldol reaction between enolisable aldehydes (donor aldehydes) and nonenolisable aldehydes (acceptor aldehydes) is known to be catalysed by L-proline and the related amine catalysts, giving antz -aldol adducts. For instance, the cross-aldol reaction of propanal with 4-nitrobenzaldehyde gave the corresponding anti-dXdoX adduct with excellent diastereo- and enantioselectivity (Scheme 17.4). ° The reaction catalysed by an amino sulfonamide (5 )-3, on the other hand, gave the unusual q n-aldol product as the major diastereomer. ... 

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