Pyrrolidinones derived from (S)-pyroglutamic acid. Part 3. β-Aminopyrrolidinones

Philip W.H. Chan; Ian F. Cottrell; Mark G. Moloney

doi:10.1039/b106782f

Pyrrolidinones derived from (S)-pyroglutamic acid. Part 3. β-Aminopyrrolidinones

Philip W.H. Chan
, Ian F. Cottrell
, Mark G. Moloney

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

25 Citations (Scopus)

Abstract

The conjugate addition of activated nitrogen nucleophiles, such as hydroxylamine and hydrazine derivatives, to Ε β,β-unsaturated bicyclic lactam 1a gave the corresponding β-amino products 9a–g in good yield and excellent diastereoselectivity. These products can be manipulated to afford enantiopure β-aminopyrrolidinones of potential application as conformationally-constrained, substituted glutamate templates of well-defined stereochemistry.

Original language	English
Pages (from-to)	2997-3006
Number of pages	10
Journal	Journal of the Chemical Society, Perkin Transactions 1
Volume	1
Issue number	22
DOIs	https://doi.org/10.1039/b106782f
Publication status	Published - 25 Oct 2001
Externally published	Yes

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abstract = "The conjugate addition of activated nitrogen nucleophiles, such as hydroxylamine and hydrazine derivatives, to Ε β,β-unsaturated bicyclic lactam 1a gave the corresponding β-amino products 9a–g in good yield and excellent diastereoselectivity. These products can be manipulated to afford enantiopure β-aminopyrrolidinones of potential application as conformationally-constrained, substituted glutamate templates of well-defined stereochemistry.",

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AU - Moloney, Mark G.

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AB - The conjugate addition of activated nitrogen nucleophiles, such as hydroxylamine and hydrazine derivatives, to Ε β,β-unsaturated bicyclic lactam 1a gave the corresponding β-amino products 9a–g in good yield and excellent diastereoselectivity. These products can be manipulated to afford enantiopure β-aminopyrrolidinones of potential application as conformationally-constrained, substituted glutamate templates of well-defined stereochemistry.

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Pyrrolidinones derived from (S)-pyroglutamic acid. Part 3. β-Aminopyrrolidinones

Abstract

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