Nonracemic α-allenyl carbinols from asymmetric propargylation with the 10-trimethylsilyl-9-borabicyclo[3.3.2]decanes
(Chemical Equation Presented) The asymmetric propargylboration of aldehydes at -78°C in 98% ee). The reagents 1 are easily prepared in both enantiomeric forms with a simple Grignard procedure and air-stable borinate complexes 2. The ozonolysis of 6 proceeds smoothly through an acylsilane intermediate to give a TMS ester, which is hydrolyzed to the α-hydroxy acid quantitatively with water.
Hernandez, Eliud,Soderquist, John A.
p. 5397 - 5400
(2007/10/03)
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