Synthesis of P-stereogenic phospholene boranes via asymmetric deprotonation and ring-closing metathesis

X. Wu; P. O'Brien; F. Secci; S. Ellwood; B. Kelly

doi:10.1021/ol303253h

Synthesis of P-stereogenic phospholene boranes via asymmetric deprotonation and ring-closing metathesis

X. Wu, P. O'Brien, F. Secci, S. Ellwood, B. Kelly

Research output: Contribution to journal › Article › peer-review

Abstract

The first examples of the asymmetric synthesis of P-stereogenic vinylic phospholene boranes are described. The synthetic approach is concise and flexible. The route involves (i) asymmetric deprotonation-allylation of a dimethyl phosphine borane; (ii) telescoped regioselective deprotonation, paraformaldehyde trapping, and hydroxyl group elimination to give a diene; and (iii) ring-closing metathesis.

Original language	English
Pages (from-to)	192-195
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	1
DOIs	https://doi.org/10.1021/ol303253h
Publication status	Published - 4 Jan 2013

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abstract = "The first examples of the asymmetric synthesis of P-stereogenic vinylic phospholene boranes are described. The synthetic approach is concise and flexible. The route involves (i) asymmetric deprotonation-allylation of a dimethyl phosphine borane; (ii) telescoped regioselective deprotonation, paraformaldehyde trapping, and hydroxyl group elimination to give a diene; and (iii) ring-closing metathesis.",

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T1 - Synthesis of P-stereogenic phospholene boranes via asymmetric deprotonation and ring-closing metathesis

AU - Wu, X.

AU - O'Brien, P.

AU - Secci, F.

AU - Ellwood, S.

AU - Kelly, B.

PY - 2013/1/4

Y1 - 2013/1/4

N2 - The first examples of the asymmetric synthesis of P-stereogenic vinylic phospholene boranes are described. The synthetic approach is concise and flexible. The route involves (i) asymmetric deprotonation-allylation of a dimethyl phosphine borane; (ii) telescoped regioselective deprotonation, paraformaldehyde trapping, and hydroxyl group elimination to give a diene; and (iii) ring-closing metathesis.

AB - The first examples of the asymmetric synthesis of P-stereogenic vinylic phospholene boranes are described. The synthetic approach is concise and flexible. The route involves (i) asymmetric deprotonation-allylation of a dimethyl phosphine borane; (ii) telescoped regioselective deprotonation, paraformaldehyde trapping, and hydroxyl group elimination to give a diene; and (iii) ring-closing metathesis.

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Synthesis of P-stereogenic phospholene boranes via asymmetric deprotonation and ring-closing metathesis

Abstract

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