Investigation of the Lithiation-Trapping of an N -Boc Bispidine-Ketal:: Reactivity and Diastereoselectivity

Darren Stead; Peter O'Brien; Adam Sanderson

doi:10.1055/s-0034-1378817

Investigation of the Lithiation-Trapping of an N -Boc Bispidine-Ketal: Reactivity and Diastereoselectivity

Darren Stead, Peter O'Brien^*, Adam Sanderson

^*Corresponding author for this work

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

Abstract

The lithiation-trapping of an N-Boc bispidine-ketal using s-BuLi/TMEDA has been studied. Key findings include an activating effect of the 4-ketal group on the lithiation and complete diastereoselectivity with methylation and Cu-mediated allylation. In contrast, reduced diastereoselectivity was noted for direct allylation and silylation; mechanistic explanations are proposed.

Original language	English
Pages (from-to)	2381-2384
Number of pages	4
Journal	Synlett
Volume	26
Issue number	17
DOIs	https://doi.org/10.1055/s-0034-1378817
Publication status	Published - 8 Jul 2015

Keywords

bispidines
diastereoselectivity
lithiation
organolithium reagents
stereoselective synthesis

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10.1055/s-0034-1378817

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AB - The lithiation-trapping of an N-Boc bispidine-ketal using s-BuLi/TMEDA has been studied. Key findings include an activating effect of the 4-ketal group on the lithiation and complete diastereoselectivity with methylation and Cu-mediated allylation. In contrast, reduced diastereoselectivity was noted for direct allylation and silylation; mechanistic explanations are proposed.

KW - bispidines

KW - diastereoselectivity

KW - lithiation

KW - organolithium reagents

KW - stereoselective synthesis

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ER -

Investigation of the Lithiation-Trapping of an N -Boc Bispidine-Ketal: Reactivity and Diastereoselectivity

Abstract

Keywords

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