Synthesis 2012; 44(14): 2138-2146
DOI: 10.1055/s-0031-1290301
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Dehydrative C-, N-, and O-Allylation Using Naph-diPIM-dioxo-i-Pr–CpRu/p-TsOH Combined Catalyst

Kengo Miyata
Research Center for Materials Science and Department of Chemistry, Nagoya University, Chikusa, Nagoya 464-8602, Japan, Fax: +81(52)7892958   Email: [email protected]
,
Masato Kitamura*
Research Center for Materials Science and Department of Chemistry, Nagoya University, Chikusa, Nagoya 464-8602, Japan, Fax: +81(52)7892958   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 26 December 2011

Accepted after revision: 01 February 2012

Publication Date:
03 April 2012 (online)


Abstract

(S,S)- or (R,R)-Naph-diPIM-dioxo-i-Pr–CpRu(II) complex with a Brønsted acid catalyzes dehydrative intermolecular C-allylation with high enantio- and regioselectivity. The new soft Ru/hard H+ combined catalyst can also be used for intramolecular C-, N-, and O-allylations, giving nearly enantiomerically pure α-alkenyl-substituted cyclic compounds. As water is only the co-product, the synthetic process can be readily scaled up.

 
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