The fate of the tert-butylsulfinyl auxiliary after acid-promoted cleavage—a method for recycling t-BuSONH 2
VK Aggarwal, N Barbero, EM McGarrigle, G Mickle…
Index: Aggarwal, Varinder K.; Barbero, Nekane; McGarrigle, Eoghan M.; Mickle, Greg; Navas, Raquel; Suarez, Jose Ramon; Unthank, Matthew G.; Yar, Muhammad Tetrahedron Letters, 2009 , vol. 50, # 26 p. 3482 - 3484
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Citation Number: 29
Abstract
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 LiNH2.
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