An Approach to Preparation of trans-DHQs via Ring-Opening of meso-N-Sulfonylaziridines: Preparation of trans-DHQs

Jens Mortansson Jelstrup Nolsøe; David Riegert; Paul Müller; David Ackland Tanner

doi:10.1135/cccc2011013

An Approach to Preparation of trans-DHQs via Ring-Opening of meso-N-Sulfonylaziridines: Preparation of trans-DHQs

Jens Mortansson Jelstrup Nolsøe, David Riegert, Paul Müller, David Ackland Tanner

Department of Chemistry

University of Geneva

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

As an approach to the enantioselective synthesis of trans-decahydroquinolines (DHQs), desymmetrization of meso-aziridine (5) with various carbon nucleophiles under catalytic conditions was investigated. By applying TMSCN in the presence of YbCl3 and chiral nonracemic ligands, nitrile 13 was obtained with an ee up to 40%. Nitrile 13 was a key intermediate in a novel route to trans-DHQs.

Original language	English
Journal	Collection of Czechoslovak Chemical Communications
Volume	76
Issue number	7
Pages (from-to)	815-828
ISSN	0010-0765
DOIs	https://doi.org/10.1135/cccc2011013
Publication status	Published - 2011

Bibliographical note

Dedicated to Professor Pavel Kočovský on the occasion of his 60th birthday.

Keywords

Synthetic methods
Alkaloids
Desymmetrization
Metathesis
trans-DHQs
Yb-catalysis
meso-Aziridines

Access to Document

10.1135/cccc2011013

OpenUrl availability

Full text

Cite this

@article{88ce8fd4c9e1407fb702fc5d81ec691e,

title = "An Approach to Preparation of trans-DHQs via Ring-Opening of meso-N-Sulfonylaziridines: Preparation of trans-DHQs",

abstract = "As an approach to the enantioselective synthesis of trans-decahydroquinolines (DHQs), desymmetrization of meso-aziridine (5) with various carbon nucleophiles under catalytic conditions was investigated. By applying TMSCN in the presence of YbCl3 and chiral nonracemic ligands, nitrile 13 was obtained with an ee up to 40%. Nitrile 13 was a key intermediate in a novel route to trans-DHQs.",

keywords = "Synthetic methods, Alkaloids, Desymmetrization, Metathesis, trans-DHQs, Yb-catalysis, meso-Aziridines, Carbon nucleophiles",

author = "Nols{\o}e, {Jens Mortansson Jelstrup} and David Riegert and Paul M{\"u}ller and Tanner, {David Ackland}",

note = "Dedicated to Professor Pavel Ko{\v c}ovsk{\'y} on the occasion of his 60th birthday.",

year = "2011",

doi = "10.1135/cccc2011013",

language = "English",

volume = "76",

pages = "815--828",

journal = "Collection of Czechoslovak Chemical Communications",

issn = "0010-0765",

publisher = "Akademie Ved Ceske Republiky Ustav Organicke Chemie a Biochemie",

number = "7",

}

TY - JOUR

T1 - An Approach to Preparation of trans-DHQs via Ring-Opening of meso-N-Sulfonylaziridines

T2 - Preparation of trans-DHQs

AU - Nolsøe, Jens Mortansson Jelstrup

AU - Riegert, David

AU - Müller, Paul

AU - Tanner, David Ackland

N1 - Dedicated to Professor Pavel Kočovský on the occasion of his 60th birthday.

PY - 2011

Y1 - 2011

N2 - As an approach to the enantioselective synthesis of trans-decahydroquinolines (DHQs), desymmetrization of meso-aziridine (5) with various carbon nucleophiles under catalytic conditions was investigated. By applying TMSCN in the presence of YbCl3 and chiral nonracemic ligands, nitrile 13 was obtained with an ee up to 40%. Nitrile 13 was a key intermediate in a novel route to trans-DHQs.

AB - As an approach to the enantioselective synthesis of trans-decahydroquinolines (DHQs), desymmetrization of meso-aziridine (5) with various carbon nucleophiles under catalytic conditions was investigated. By applying TMSCN in the presence of YbCl3 and chiral nonracemic ligands, nitrile 13 was obtained with an ee up to 40%. Nitrile 13 was a key intermediate in a novel route to trans-DHQs.

KW - Synthetic methods

KW - Alkaloids

KW - Desymmetrization

KW - Metathesis

KW - trans-DHQs

KW - Yb-catalysis

KW - meso-Aziridines

KW - Carbon nucleophiles

U2 - 10.1135/cccc2011013

DO - 10.1135/cccc2011013

M3 - Journal article

SN - 0010-0765

VL - 76

SP - 815

EP - 828

JO - Collection of Czechoslovak Chemical Communications

JF - Collection of Czechoslovak Chemical Communications

IS - 7

ER -

An Approach to Preparation of trans-DHQs via Ring-Opening of meso-N-Sulfonylaziridines: Preparation of trans-DHQs

Abstract

Bibliographical note

Keywords

Access to Document

OpenUrl availability

Fingerprint

Cite this