Method for Catalytic Enantioselective Alkylation of Aldehydes Using Grignard Reagents as Alkyl Sources

Alkyltitanium reagents, generated in situ from Grignard reagents and ClTi­(O i Pr)3, can be employed without further manipulation in the enantioselective alkylation of aldehyde by the catalysis of a chiral titanium complex derived from DTBP-H8-BINOL. The reaction is performed with good stoichiometry...

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Veröffentlicht in:Journal of organic chemistry 2018-06, Vol.83 (11), p.6127-6132
Hauptverfasser: Tanaka, Kento, Tomihama, Munehisa, Yamamoto, Koji, Matsubara, Naoki, Harada, Toshiro
Format: Artikel
Sprache:eng
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Zusammenfassung:Alkyltitanium reagents, generated in situ from Grignard reagents and ClTi­(O i Pr)3, can be employed without further manipulation in the enantioselective alkylation of aldehyde by the catalysis of a chiral titanium complex derived from DTBP-H8-BINOL. The reaction is performed with good stoichiometry [1.5 equiv each of Grignard reagents and ClTi­(O i Pr)3] at a low catalyst loading (2 mol %), affording a variety of chiral secondary alcohols in high enantioselectivity and yields and, hence, realizing an asymmetric version of the Grignard reaction in an indirect manner.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00929