Stereoselective synthesis of 2-dienyl-substituted pyrrolidines using an η4-dienetricarbonyliron complex as the stereodirecting element: Elaboration to the pyrrolizidine skeleton

Iwan Williams; Benson M. Kariuki; Keith Reeves; Liam R. Cox

doi:10.1021/ol061132l

Stereoselective synthesis of 2-dienyl-substituted pyrrolidines using an η⁴-dienetricarbonyliron complex as the stereodirecting element: Elaboration to the pyrrolizidine skeleton

Iwan Williams, Benson M. Kariuki, Keith Reeves, Liam R. Cox^*

^*Corresponding author for this work

Chemistry

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

16 Citations (Scopus)

Abstract

Primary amines react with keto-aldehyde functionality located in the side-chain of an η⁴-dienetricarbonyliron complex to provide the corresponding pyrrolidines in excellent diastereoselectivity. Two of the pyrrolidine products, 1i and 1k, have been elaborated into pyrrolizidines using a 1,5-C-H insertion and radical cyclization strategy, respectively.

Original language	English
Pages (from-to)	4389-4392
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	20
DOIs	https://doi.org/10.1021/ol061132l
Publication status	Published - 28 Sept 2006

ASJC Scopus subject areas

Biochemistry
General Medicine
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol061132l

Cite this

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abstract = "Primary amines react with keto-aldehyde functionality located in the side-chain of an η4-dienetricarbonyliron complex to provide the corresponding pyrrolidines in excellent diastereoselectivity. Two of the pyrrolidine products, 1i and 1k, have been elaborated into pyrrolizidines using a 1,5-C-H insertion and radical cyclization strategy, respectively.",

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AU - Kariuki, Benson M.

AU - Reeves, Keith

AU - Cox, Liam R.

PY - 2006/9/28

Y1 - 2006/9/28

N2 - Primary amines react with keto-aldehyde functionality located in the side-chain of an η4-dienetricarbonyliron complex to provide the corresponding pyrrolidines in excellent diastereoselectivity. Two of the pyrrolidine products, 1i and 1k, have been elaborated into pyrrolizidines using a 1,5-C-H insertion and radical cyclization strategy, respectively.

AB - Primary amines react with keto-aldehyde functionality located in the side-chain of an η4-dienetricarbonyliron complex to provide the corresponding pyrrolidines in excellent diastereoselectivity. Two of the pyrrolidine products, 1i and 1k, have been elaborated into pyrrolizidines using a 1,5-C-H insertion and radical cyclization strategy, respectively.

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