Journal of Organic Chemistry 2009-08-21

Synthesis of highly enantioenriched chiral alpha-aminoorganotins via diastereoselective ring opening of chiral N-(arenesulfonyl) 2-tributylstannyloxazolidines.

Vincent Coeffard, Erwan Le Grognec, Isabelle Beaudet, Michel Evain, Jean-Paul Quintard

Index: J. Org. Chem. 74(16) , 5822-38, (2009)

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Abstract

trans-N-(Arenesulfonyl)-2-tributylstannyloxazolidines derived from (R)-phenylglycinol were diastereoselectively ring-opened by soft organometallic reagents in the presence of BF(3).OEt(2). Both higher order organocuprates and allyltributyltin afforded the desired products in good-to-excellent yields and high diastereoselectivities (dr up to 99/1). The stereochemical assignments of tributylstannyl-beta-aminoalcohols were firmly established from NMR data and after determination of several radiocrystallographic structures. Mechanisms were proposed in order to rationalize the observed selectivities.