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. Author manuscript; available in PMC: 2010 Jul 1.
Published in final edited form as: J Am Chem Soc. 2009 Jul 1;131(25):9038–9045. doi: 10.1021/ja902677t

Scheme 5.

Scheme 5

Diastereoselective Propargylation of Aldehyde 25.a

aReagents and Conditions: a) DIBAL, CH2Cl2, −78 °C, 96%; b) TPAP, NMO, 4Å MS, CH2Cl2, 99%; c) SnCl4, CH2Cl2, −78 °C d) Propargyl bromide, Mg0, HgCl2, Et2O, −20 °C, 96%, dr = 84:16.