Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 30, Pages 10364-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9041127
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Funding
- NIGMS NIH HHS [R01 GM074822, R01-GM074822, R01 GM074822-05] Funding Source: Medline
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Unsymmetricalty substituted allenes (1,2-dienes) are inherently chiral and can be prepared in optically pure form. Nonetheless, to date the allene framework has not been incorporated into ligands for asymmetric catalysis. Since allenes project functionality differently than either tetrahedral carbon or chiral biaryls, they may create complementary chiral environments. This study demonstrates that optically active, C-2-symmetric allene-containing bisphosphine oxides can catalyze the addition of SiCl4 to meso-epoxides with high enantioselectivity. The epoxide opening likely involves generation of a Lewis acidic, cationic (bisphosphine oxide)SiCl3 complex. The fact that high asymmetric induction is observed suggests that allenes may represent a new platform for the development of ligands and catalysts for asymmetric synthesis.
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