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Highly Diastereoselective Addition of Alkynylmagnesium Chlorides to N-tert-Butanesulfinyl Aldimines: A Practical and General Access to Chiral α-Branched Amines

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posted on 05.02.2010, 00:00 by Bai-Ling Chen, Bing Wang, Guo-Qiang Lin
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 α-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.