Highly Diastereoselective Addition of Alkynylmagnesium Chlorides to N-tert-Butanesulfinyl Aldimines: A Practical and General Access to Chiral α-Branched Amines
The Journal of Organic Chemistry2009Vol. 75(3), pp. 941–944
Citations Over TimeTop 11% of 2009 papers
Abstract
The addition of alkynylmagnesium chlorides to N-tert-butanesulfinyl imines proceeded with a remarkably high diastereoselectivity (dr > 13:1, mostly diastereopure), and with a general scope of both reaction partners. The high dr translated into simplified purification and higher optical purity for the synthesis of a wide array of chiral alpha-branched amines. The alkyne functionality also provides a multitude of opportunities for further synthetic transformations. The short asymmetric synthesis of (+)-angustureine 7 and (-)-cuspareine 10 was realized with use of this approach.
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