A new diastereoselective aza-allyl conjugate addition-Michael addition-ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres

M Koutsaplis; P C Andrews; S D Bull; P J Duggan; B H Fraser; P Jensen

doi:10.1039/b707707f

A new diastereoselective aza-allyl conjugate addition-Michael addition-ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres

M Koutsaplis, P C Andrews, S D Bull, P J Duggan, B H Fraser, P Jensen

Department of Chemistry

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

21 Citations (SciVal)

Abstract

Reaction of the sodium anion of (S)-N-(alpha-methylbenzyl)allylamine with two equivalents of tert-butyl cinnamate results in a remarkable tandem aza-allyl conjugate addition-Michael addition-ring closure reaction, resulting in a chiral aminocyclohexane containing six new vicinal stereogenic centres with excellent levels of stereocontrol.

Original language	English
Pages (from-to)	3580-3582
Number of pages	3
Journal	Chemical Communications
Issue number	34
DOIs	https://doi.org/10.1039/b707707f
Publication status	Published - 2007

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ID number: ISI:000249588400028

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10.1039/b707707f

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title = "A new diastereoselective aza-allyl conjugate addition-Michael addition-ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres",

abstract = "Reaction of the sodium anion of (S)-N-(alpha-methylbenzyl)allylamine with two equivalents of tert-butyl cinnamate results in a remarkable tandem aza-allyl conjugate addition-Michael addition-ring closure reaction, resulting in a chiral aminocyclohexane containing six new vicinal stereogenic centres with excellent levels of stereocontrol.",

author = "M Koutsaplis and Andrews, {P C} and Bull, {S D} and Duggan, {P J} and Fraser, {B H} and P Jensen",

note = "ID number: ISI:000249588400028",

year = "2007",

doi = "10.1039/b707707f",

language = "English",

pages = "3580--3582",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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T1 - A new diastereoselective aza-allyl conjugate addition-Michael addition-ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres

AU - Koutsaplis, M

AU - Andrews, P C

AU - Bull, S D

AU - Duggan, P J

AU - Fraser, B H

AU - Jensen, P

N1 - ID number: ISI:000249588400028

PY - 2007

Y1 - 2007

N2 - Reaction of the sodium anion of (S)-N-(alpha-methylbenzyl)allylamine with two equivalents of tert-butyl cinnamate results in a remarkable tandem aza-allyl conjugate addition-Michael addition-ring closure reaction, resulting in a chiral aminocyclohexane containing six new vicinal stereogenic centres with excellent levels of stereocontrol.

AB - Reaction of the sodium anion of (S)-N-(alpha-methylbenzyl)allylamine with two equivalents of tert-butyl cinnamate results in a remarkable tandem aza-allyl conjugate addition-Michael addition-ring closure reaction, resulting in a chiral aminocyclohexane containing six new vicinal stereogenic centres with excellent levels of stereocontrol.

U2 - 10.1039/b707707f

DO - 10.1039/b707707f

M3 - Article

SN - 1359-7345

SP - 3580

EP - 3582

JO - Chemical Communications

JF - Chemical Communications

IS - 34

ER -

A new diastereoselective aza-allyl conjugate addition-Michael addition-ring closure reaction sequence and its application in the construction of six contiguous stereogenic centres

Abstract

Bibliographical note

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