Tert-butanesulfinyl chloride

At around the same time, Ellman and coworkers [52] also reported similar results for anchona-catalyzed sulfinyl transfer reactions to those obtained by the Shibata group [51]. They found that the parent anchona alkaloids effectively catalyzed the sulfinyl transfer reaction of tert-butanesulfinyl chloride (rac-74) and a variety ofbenzyl alcohols in the presence of a proton sponge (2.5 equiv). For example, in the presence of 10 mol% of quinidine (2) and 2.5 equivalents of a proton sponge, sulfinyl transfer with 2,4,6-trichlorobenzyl alcohol (77) provided the sulftnate ester 78 in 92% yield and with 90% ee (Scheme 11.37). 

Scheme 2.111 Quinidine-catalysed DKR of tert-butanesulfinyl chloride.

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