Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Phosphine Oxide-Catalyzed Asymmetric Aldol Reactions and Double Aldol Reactions
Shunsuke Kotani
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2019 年 67 巻 6 号 p. 519-526

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Chiral phosphine oxides successfully catalyze asymmetric cross-aldol reactions of various carbonyl compounds in a highly enantioselective manner. The phosphine oxide catalysts coordinate to chlorosilanes to form chiral hypervalent silicon complexes in situ, which activate both aldol donors and acceptors, thus realizing cross-aldol reactions between a ketone and an aldehyde, between two aldehydes, between two ketones, and of 2,6-diketones. The use of phosphine oxide catalysis can be further extended to achieve the first catalytic enantioselective double aldol reactions, realizing one-pot stereoselective construction of up to four stereogenic centers.

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© 2019 The Pharmaceutical Society of Japan
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