A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives.

S M  Allin; C J  Northfield; M I  Page; A M Z  Slawin

A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives.

S M Allin, C J Northfield, M I Page, A M Z Slawin

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

Abstract

Condensation of 2-formylbenzoic acid with alpha-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic gamma-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical outcome. Further, we report that this class of heterocycle can act as an N-acyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives. (C) 1997 Elsevier Science Ltd.

Original language	English
Pages (from-to)	3627-3630
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	20
Publication status	Published - 19 May 1997

Keywords

SIMPLE ASYMMETRIC-SYNTHESIS
2-SUBSTITUTED PYRROLIDINES

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title = "A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives.",

abstract = "Condensation of 2-formylbenzoic acid with alpha-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic gamma-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical outcome. Further, we report that this class of heterocycle can act as an N-acyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives. (C) 1997 Elsevier Science Ltd.",

keywords = "SIMPLE ASYMMETRIC-SYNTHESIS, 2-SUBSTITUTED PYRROLIDINES",

author = "Allin, {S M} and Northfield, {C J} and Page, {M I} and Slawin, {A M Z}",

year = "1997",

month = may,

day = "19",

language = "English",

volume = "38",

pages = "3627--3630",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives.

AU - Allin, S M

AU - Northfield, C J

AU - Page, M I

AU - Slawin, A M Z

PY - 1997/5/19

Y1 - 1997/5/19

N2 - Condensation of 2-formylbenzoic acid with alpha-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic gamma-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical outcome. Further, we report that this class of heterocycle can act as an N-acyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives. (C) 1997 Elsevier Science Ltd.

AB - Condensation of 2-formylbenzoic acid with alpha-amino alcohol substrates proceeds with extremely high diastereoselectivity to produce tricyclic gamma-lactam products. The relative stereochemistry of the major diastereoisomer has been determined by X-ray crystal analysis and a mechanism suggested to explain the stereochemical outcome. Further, we report that this class of heterocycle can act as an N-acyl iminium ion precursor in the synthesis of substituted isoindolinone derivatives. (C) 1997 Elsevier Science Ltd.

KW - SIMPLE ASYMMETRIC-SYNTHESIS

KW - 2-SUBSTITUTED PYRROLIDINES

M3 - Article

SN - 0040-4039

VL - 38

SP - 3627

EP - 3630

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 20

ER -

A highly diastereoselective synthesis of tricyclic lactams and their application as novel N-acyl iminium ion precursors in the synthesis of isoindolinone derivatives.

Abstract

Keywords

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