Kinetic resolution of terminal epoxides via highly regioselective and enantioselective ring opening with TMSN3. An efficient, catalytic route to 1, 2-amino alcohols

…, SE Schaus, EN Jacobsen

Index: Larrow, Jay F.; Schaus, Scott E.; Jacobsen, Eric N. Journal of the American Chemical Society, 1996 , vol. 118, # 31 p. 7420 - 7421

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Citation Number: 230

Abstract

The value of enantiopure 1, 2-amino alcohols lies in their utility both as intermediates for the synthesis of a wide range of biologically important compounds1 and as precursors to effective and versatile ligands for asymmetric catalysis. 2 Existing synthetic routes to amino alcohols rely heavily on the chiral pool, 2b and particularly on the reduction of R-amino acids. While this approach provides ready access to many 2-amino-1-ols, the ...