Applications of tert-butanesulfinamide in the asymmetric
synthesis of amines
J. A. Ellman
Center for New Directions in Organic Synthesis, Department
of Chemistry, University of California at Berkeley, Berkeley, CA 94720,
USA
Abstract: tert-Butanesulfinamide is prepared using catalytic
enantioselective methods in two steps from the extremely inexpensive
oil waste by-product, tert-butyl disulfide. Direct condensation
of tert-butanesulfinamide with aldehydes and ketones provides
tert-butanesulfinyl imines in uniformly high yields. The tert-butanesulfinyl
group activates the imines for the addition of many different classes
of nucleophiles, serves as a powerful chiral directing group, and after
nucleophilic addition is readily cleaved by treatment with acid. A wide
range of highly enantioenriched amines, including
a-branched and a,a-dibranched
amines, a- and b-amino
acids, 1,2 and 1,3-amino alcohols and a-trifluoromethyl
amines are efficiently synthesized using this methodology.
*Lecture presented at the 14th International Conference
on Organic Synthesis (ICOS-14), Christchurch, New Zealand, 14-18 July
2002. Other presentations are published in this issue,
pp. 1-70.
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