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Pure Appl. Chem., 2013, Vol. 85, No. 6, pp. 1121-1132

Published online 2013-04-15

CpRu-catalyzed asymmetric dehydrative allylation

Masato Kitamura1*, Kengo Miyata2, Tomoaki Seki3, Namdev Vatmurge2 and Shinji Tanaka2

1 Graduate School of Pharmaceutical Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan
2 Research Center for Materials Science, Nagoya University, Chikusa, Nagoya 464-8601, Japan
3 Graduate School of Science, Nagoya University, Chikusa, Nagoya 464-8601, Japan

Abstract: Asymmetric Tsuji–Trost allylation is one of the key chiral technologies for construction of pharmaceutically important compounds because of the high utility of alkenyl-substituted products. Particularly, the dehydrative system using allylic alcohols and protic nucleophiles has started to attract the attention of organic synthetic chemists from the viewpoints of atom and step economy, environmental benignity, and operational simplicity. In this paper, two types of new chiral CpRu catalysts, which have been developed on the basis of redox-mediated donor–acceptor bifunctional catalyst (RDACat) concept, are presented. Complementary use of the chiral catalysts has realized the syntheses of a wide rage of carbocyclic compounds, saturated N- or O-heterocyclic compounds with high reactivity, regioselectivity, enantioselectivity, productivity, and generality.