N-acyl 'Quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis

Stephen G. Davies; Darren J. Dixon

doi:10.1039/b205326h

N-acyl 'Quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis

Stephen G. Davies, Darren J. Dixon

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

Abstract

A novel route to chiral amides through the efficient, non-racemising, cleavage of N-acyl side chains from a 'Quat' chiral auxiliary using N-centred nucleophiles is described. The synthetic utility of the procedure is then highlighted by the preparation of a range of succinamide and succinimide derivatives and through the synthesis of the natural product (S)-(+)-amphetamine via a stereospecific Hofman type degradation using a hypervalent iodine reagent.

Original language	English
Pages (from-to)	1869-1876
Number of pages	7
Journal	Journal of the Chemical Society. Perkin Transactions 1
Issue number	16
DOIs	https://doi.org/10.1039/b205326h
Publication status	Published - 2002

Keywords

Aminolysis; Chiral auxiliary; Hofmann degradation; Stereoselective synthesis (prepn. of amides by direct aminolysis/Hofmann degrdn. of N-acylpyrrolidinone as chiral auxiliary); Amides Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of amides by direct aminolysis/Hofmann degrdn. of N-acylpyrrolidinone as chiral auxiliary)

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10.1039/b205326h

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title = "N-acyl 'Quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis",

abstract = "A novel route to chiral amides through the efficient, non-racemising, cleavage of N-acyl side chains from a 'Quat' chiral auxiliary using N-centred nucleophiles is described. The synthetic utility of the procedure is then highlighted by the preparation of a range of succinamide and succinimide derivatives and through the synthesis of the natural product (S)-(+)-amphetamine via a stereospecific Hofman type degradation using a hypervalent iodine reagent.",

keywords = "Aminolysis; Chiral auxiliary; Hofmann degradation; Stereoselective synthesis (prepn. of amides by direct aminolysis/Hofmann degrdn. of N-acylpyrrolidinone as chiral auxiliary); Amides Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of amides by direct aminolysis/Hofmann degrdn. of N-acylpyrrolidinone as chiral auxiliary)",

author = "Davies, \{Stephen G.\} and Dixon, \{Darren J.\}",

year = "2002",

doi = "10.1039/b205326h",

language = "English",

pages = "1869--1876",

journal = "Journal of the Chemical Society. Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "16",

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T1 - N-acyl 'Quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis

AU - Davies, Stephen G.

AU - Dixon, Darren J.

PY - 2002

Y1 - 2002

N2 - A novel route to chiral amides through the efficient, non-racemising, cleavage of N-acyl side chains from a 'Quat' chiral auxiliary using N-centred nucleophiles is described. The synthetic utility of the procedure is then highlighted by the preparation of a range of succinamide and succinimide derivatives and through the synthesis of the natural product (S)-(+)-amphetamine via a stereospecific Hofman type degradation using a hypervalent iodine reagent.

AB - A novel route to chiral amides through the efficient, non-racemising, cleavage of N-acyl side chains from a 'Quat' chiral auxiliary using N-centred nucleophiles is described. The synthetic utility of the procedure is then highlighted by the preparation of a range of succinamide and succinimide derivatives and through the synthesis of the natural product (S)-(+)-amphetamine via a stereospecific Hofman type degradation using a hypervalent iodine reagent.

KW - Aminolysis; Chiral auxiliary; Hofmann degradation; Stereoselective synthesis (prepn. of amides by direct aminolysis/Hofmann degrdn. of N-acylpyrrolidinone as chiral auxiliary); Amides Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of amides

UR - https://www.scopus.com/pages/publications/0035982155

U2 - 10.1039/b205326h

DO - 10.1039/b205326h

M3 - Article

SN - 1472-7781

SP - 1869

EP - 1876

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

IS - 16

ER -

N-acyl 'Quat' pyrrolidinone auxiliary as a chiral amide equivalent via direct aminolysis

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Keywords

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