910787-21-2Relevant academic research and scientific papers
B-allenyl- and B-(γ-trimethylsilylpropargyl)-10-phenyl-9- borabicyclo[3.3.2]decanes: Asymmetric synthesis of propargyl and α-allenyl 3°-carbinols from ketones
Hernandez, Eliud,Burgos, Carlos H.,Alicea, Eyleen,Soderquist, John A.
, p. 4089 - 4091 (2006)
Simple and efficient Grignard procedures are reported for the syntheses of B-allenyl-10-(phenyl)-9-borabicyclo[3.3.2]decane (1) and its B-(γ-trimethylsilylpropargyl) counterpart (2) in both enantiomeric forms. Both add selectively to ketones, providing propargyl- and α-silylallenyl 3°-carbinols, respectively (i.e., 6 (61-93% ee) and 9 (64-98% ee)). The air-stable boron byproduct is efficiently recovered and recycled back to either 1 or 2. The ozonolysis and bromination of 9 provide nonracemic α-hydroxy acids and γ-bromopropynyl carbinols, respectively.
