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. 2002 Oct 31;4(22):3827-30.
doi: 10.1021/ol026619i.

A mild protocol for allylation and highly diastereoselective syn or anti crotylation of aldehydes in biphasic and aqueous media utilizing potassium allyl- and crotyltrifluoroborates

Avinash N Thadani  1 , Robert A Batey
Affiliations

A mild protocol for allylation and highly diastereoselective syn or anti crotylation of aldehydes in biphasic and aqueous media utilizing potassium allyl- and crotyltrifluoroborates

Avinash N Thadani et al. Org Lett. .

Abstract

[formula: see text] Potassium allyl- and crotyltrifluoroborates undergo addition to aldehydes in biphasic media as well as water to provide the corresponding homoallylic alcohols in high yields (> or = 94%), excellent diastereoselectivity (dr > or = 98:2), and without the necessity of any subsequent purification. The presence of a phase transfer catalyst (e.g., nBu4NI) significantly accelerates the rate of reaction, whereas added fluoride ion retards the reaction.

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