tert-Butanesulfinamide (also known as 2-methyl-2-propanesulfinamide or Ellman's sulfinamide) is an organosulfur compound and a member of the class of sulfinamides. Both enantiomeric forms are commercially available and are used in asymmetric synthesis as chiral auxiliaries , often as chiral ammonia equivalents for the synthesis of amines .

Ellman's sulfinamide is available in both enantiomeric and racemic forms for your research. This versatile and useful auxiliary has found extensive use both in academics and industry.

In 1997, Ellman reported the enantioselective synthesis and application of tert-butanesulfinamide for the preparation of enantioenriched amines. R1 = p-tolyl (Davis), tert-butyl (Ellman). Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913–9914.

Chiral auxiliaries are one of many strategies available to synthetic chemists to selectively produce the desired stereoisomer of a given compound. [4] Chiral auxiliaries were introduced by Elias James Corey in 1975 [5] with chiral 8-phenylmenthol …

The Ellman lab continues to develop sustainable and highly functional group compatible approaches for the synthesis of diverse classes of amines from readily available starting materials. In one major approach, the lab utilizes catalytic C-H bond functionalization (discussed in the C-H Functionalization research section).

Ellman’s chiral auxiliary is converted into tert-butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can

Chiral sulfinamides are among the best known chiral auxiliaries in the stereoselective synthesis of amines and their derivatives. The most extensively used enantiopure tert -butanesulfinamide emerged as the gold standard among many others over the last two decades.

The tert-butanesulfinyl group not only is an ideal auxiliary for the synthesis of β-amino esters but also can serve as a versatile, low-molecular-weight protecting group analogous to the Boc protecting group. First, the tert-butanesulfinyl group is stable to …

We are interested in the application of Ellman’s N-tert-butanesulfinyl chiral auxiliary in the development of new enantioselective synthetic methods.

2009年7月1日 · Ellman’s chiral auxiliary is converted into tert -butylsulfinyl chloride on sulfinamide deprotection with HCl and can be recovered in high yield upon treatment with ammonia. The enantiopure auxiliary can be obtained by trapping the sulfinyl chloride with a chiral alcohol followed by treatment of the resulting sulfinate ester with LiNH 2.