期刊
ORGANIC LETTERS
卷 8, 期 18, 页码 4089-4091出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol061596j
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资金
- NIGMS NIH HHS [S06 GM 8102, S06 GM008102-320051, S06 GM008102] Funding Source: Medline
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-(gamma-trimethylsilylpropargyl) counterpart (2) in both enantiomeric forms. Both add selectively to ketones, providing propargyl- and alpha-silylallenyl 3 degrees-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 alpha-hydroxy acids and gamma-bromopropynyl carbinols, respectively.
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