A Novel Asymmetric Azaspirocyclisation Using a Morita-Baylis-Hillman-Type Reaction

Jonathan C. Killen; John Leonard; Varinder K. Aggarwal

doi:10.1055/s-0029-1219210

A Novel Asymmetric Azaspirocyclisation Using a Morita-Baylis-Hillman-Type Reaction

Jonathan C. Killen, John Leonard, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

11 Citations (Scopus)

Abstract

A Morita-Baylis-Hillman-type reaction has been applied to the asymmetric preparation of azaspirocycles in high yield and diastereoselectivity. The optimisation of the reaction is discussed and a model for the origin of diastereoselectivity is proposed.

Original language	English
Pages (from-to)	579-582
Number of pages	4
Journal	SYNLETT
Issue number	4
DOIs	https://doi.org/10.1055/s-0029-1219210
Publication status	Published - Mar 2010

Keywords

Morita-Baylis-Hillman-type reaction
azaspirocyclisation
spiro compounds
asymmetric synthesis
diastereoselectivity
ASCIDIAN CLAVELINA-CYLINDRICA
STEREOSELECTIVE ALPHA-AMIDOALKYLATION
ACYLIMINIUM ION CYCLIZATIONS
BICYCLIC LACTAMS
ENANTIOSELECTIVE SYNTHESIS
SPIRO 2-PYRROLIDIN-5-ONES
DENDROBATES-HISTRIONICUS
NEOTROPICAL FROG
SYNTHETIC ROUTE
ALKALOIDS

Access to Document

10.1055/s-0029-1219210

Handle.net

Persistent link

NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/05 → 1/10/10
Project: Research

Cite this

@article{d3898de126844f3ea8d602381cf18bd8,

title = "A Novel Asymmetric Azaspirocyclisation Using a Morita-Baylis-Hillman-Type Reaction",

abstract = "A Morita-Baylis-Hillman-type reaction has been applied to the asymmetric preparation of azaspirocycles in high yield and diastereoselectivity. The optimisation of the reaction is discussed and a model for the origin of diastereoselectivity is proposed.",

keywords = "Morita-Baylis-Hillman-type reaction, azaspirocyclisation, spiro compounds, asymmetric synthesis, diastereoselectivity, ASCIDIAN CLAVELINA-CYLINDRICA, STEREOSELECTIVE ALPHA-AMIDOALKYLATION, ACYLIMINIUM ION CYCLIZATIONS, BICYCLIC LACTAMS, ENANTIOSELECTIVE SYNTHESIS, SPIRO 2-PYRROLIDIN-5-ONES, DENDROBATES-HISTRIONICUS, NEOTROPICAL FROG, SYNTHETIC ROUTE, ALKALOIDS",

author = "Killen, {Jonathan C.} and John Leonard and Aggarwal, {Varinder K.}",

year = "2010",

month = mar,

doi = "10.1055/s-0029-1219210",

language = "English",

pages = "579--582",

journal = "SYNLETT",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "4",

}

TY - JOUR

T1 - A Novel Asymmetric Azaspirocyclisation Using a Morita-Baylis-Hillman-Type Reaction

AU - Killen, Jonathan C.

AU - Leonard, John

AU - Aggarwal, Varinder K.

PY - 2010/3

Y1 - 2010/3

N2 - A Morita-Baylis-Hillman-type reaction has been applied to the asymmetric preparation of azaspirocycles in high yield and diastereoselectivity. The optimisation of the reaction is discussed and a model for the origin of diastereoselectivity is proposed.

AB - A Morita-Baylis-Hillman-type reaction has been applied to the asymmetric preparation of azaspirocycles in high yield and diastereoselectivity. The optimisation of the reaction is discussed and a model for the origin of diastereoselectivity is proposed.

KW - Morita-Baylis-Hillman-type reaction

KW - azaspirocyclisation

KW - spiro compounds

KW - asymmetric synthesis

KW - diastereoselectivity

KW - ASCIDIAN CLAVELINA-CYLINDRICA

KW - STEREOSELECTIVE ALPHA-AMIDOALKYLATION

KW - ACYLIMINIUM ION CYCLIZATIONS

KW - BICYCLIC LACTAMS

KW - ENANTIOSELECTIVE SYNTHESIS

KW - SPIRO 2-PYRROLIDIN-5-ONES

KW - DENDROBATES-HISTRIONICUS

KW - NEOTROPICAL FROG

KW - SYNTHETIC ROUTE

KW - ALKALOIDS

U2 - 10.1055/s-0029-1219210

DO - 10.1055/s-0029-1219210

M3 - Article (Academic Journal)

SN - 0936-5214

SP - 579

EP - 582

JO - SYNLETT

JF - SYNLETT

IS - 4

ER -

A Novel Asymmetric Azaspirocyclisation Using a Morita-Baylis-Hillman-Type Reaction

Abstract

Keywords

Access to Document

Handle.net

Fingerprint

Projects

NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

Cite this