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 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.8b00929 |