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3-Chloro-1-lithiopropene - a functional organolithium reagent - and its reactions with alkylboronates to give 3-Alkylprop-1-en-3-ols

Smith, Keith, Elliott, Mark Christopher and Jones, Dyfyr Heulyn 2013. 3-Chloro-1-lithiopropene - a functional organolithium reagent - and its reactions with alkylboronates to give 3-Alkylprop-1-en-3-ols. Journal of Organic Chemistry 78 (18) , pp. 9526-9531. 10.1021/jo4018028

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Abstract

The reagent 3-chloro-1-lithiopropene (4) can be generated by treating 1 bromo-3-chloropropene with t-BuLi. It is unstable, but if generated at low temperature in presence of alkylboronic esters such as 3 is trapped in situ to give rearrangement products 2 (Scheme 1a), which on oxidation give 3 alkylprop-1-en-3-ols in good yields. The reaction works for primary, secondary, benzylic and even tertiary alkylboronic esters, providing allylic alcohols bearing almost any alkyl group available using organoborane chemistry and incorporating all features of such groups.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: ACS
ISSN: 0022-3263
Funders: EPSRC
Date of First Compliant Deposit: 30 March 2016
Last Modified: 04 Jun 2017 05:18
URI: http://orca.cf.ac.uk/id/eprint/50468

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