Enantioselective Synthesis of P-Stereogenic Phosphinates and Phosphine oxides by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis

被引:124
作者
Harvey, James Stephen [2 ]
Malcolmson, Steven J. [1 ]
Dunne, Katherine S. [2 ]
Meek, Simon J. [1 ]
Thompson, Amber L. [2 ]
Schrock, Richard R. [3 ]
Hoveyda, Amir H. [1 ]
Gouverneur, Veronique [2 ]
机构
[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
[2] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
[3] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家卫生研究院; 英国工程与自然科学研究理事会;
关键词
enantioselective synthesis; homogeneous catalysis; molybdenum; olefin metathesis; phosphorus; NEUTRAL COORDINATE-ORGANOCATALYSTS; OLEFIN-METATHESIS; CROSS-METATHESIS; SECONDARY PHOSPHINES; ALKYLIDENE COMPLEXES; TERTIARY ETHERS; ALLYLATION; PHOSPHORUS; DESYMMETRIZATION; HETEROCYCLES;
D O I
10.1002/anie.200805066
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) The first catalytic route toward the title compounds by asymmetric ring-closing metathesis is described. A remarkable reversal of enantioselectivity is observed when the achiral imido ligand of the chiral molybdenum-catalyst is changed (see scheme), thus highlighting the importance of the achiral and the chiral ligands in catalyst design. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:762 / 766
页数:5
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