Tactics for the asymmetric preparation of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane scaffolds

Andrzej Wolan; Mohamad Soueidan; Angèle Chiaroni; Pascal Retailleau; Sandrine Py; Yvan Six

doi:10.1016/j.tetlet.2011.03.026

Tactics for the asymmetric preparation of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane scaffolds

Andrzej Wolan
, Mohamad Soueidan
, Angèle Chiaroni
, Pascal Retailleau
, Sandrine Py
, Yvan Six

Centre national de la recherche scientifique
Département de Chimie Moléculaire
Laboratoire de Synthèse Organique

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

Abstract

In this contribution, two methods are presented for the removal of benzyl-type protecting groups attached to the nitrogen atom of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane systems. The first, based on the Polonovski reaction, is suitable for [3.1.0] systems. The second relies on an elimination process, starting from derivatives of O-methyl phenylglycinol, and is more general in terms of the substrates tolerated. Secondary bicyclic cyclopropylamines, including enantiomerically pure molecules, can thus be accessed. These compounds are then ready for further functionalisation.

Original language	English
Pages (from-to)	2501-2504
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2011.03.026
Publication status	Published - 11 May 2011

Keywords

Aminocyclopropanes
Chiral auxiliaries
Kulinkovich-de Meijere reaction
Organotitanium chemistry
Polonovski reaction

Access to Document

10.1016/j.tetlet.2011.03.026

Cite this

@article{7be9d6e60a9c4a2788d4d495c56297ff,

title = "Tactics for the asymmetric preparation of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane scaffolds",

abstract = "In this contribution, two methods are presented for the removal of benzyl-type protecting groups attached to the nitrogen atom of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane systems. The first, based on the Polonovski reaction, is suitable for [3.1.0] systems. The second relies on an elimination process, starting from derivatives of O-methyl phenylglycinol, and is more general in terms of the substrates tolerated. Secondary bicyclic cyclopropylamines, including enantiomerically pure molecules, can thus be accessed. These compounds are then ready for further functionalisation.",

keywords = "Aminocyclopropanes, Chiral auxiliaries, Kulinkovich-de Meijere reaction, Organotitanium chemistry, Polonovski reaction",

author = "Andrzej Wolan and Mohamad Soueidan and Ang{\`e}le Chiaroni and Pascal Retailleau and Sandrine Py and Yvan Six",

year = "2011",

month = may,

day = "11",

doi = "10.1016/j.tetlet.2011.03.026",

language = "English",

volume = "52",

pages = "2501--2504",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "19",

}

TY - JOUR

T1 - Tactics for the asymmetric preparation of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane scaffolds

AU - Wolan, Andrzej

AU - Soueidan, Mohamad

AU - Chiaroni, Angèle

AU - Retailleau, Pascal

AU - Py, Sandrine

AU - Six, Yvan

PY - 2011/5/11

Y1 - 2011/5/11

N2 - In this contribution, two methods are presented for the removal of benzyl-type protecting groups attached to the nitrogen atom of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane systems. The first, based on the Polonovski reaction, is suitable for [3.1.0] systems. The second relies on an elimination process, starting from derivatives of O-methyl phenylglycinol, and is more general in terms of the substrates tolerated. Secondary bicyclic cyclopropylamines, including enantiomerically pure molecules, can thus be accessed. These compounds are then ready for further functionalisation.

AB - In this contribution, two methods are presented for the removal of benzyl-type protecting groups attached to the nitrogen atom of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane systems. The first, based on the Polonovski reaction, is suitable for [3.1.0] systems. The second relies on an elimination process, starting from derivatives of O-methyl phenylglycinol, and is more general in terms of the substrates tolerated. Secondary bicyclic cyclopropylamines, including enantiomerically pure molecules, can thus be accessed. These compounds are then ready for further functionalisation.

KW - Aminocyclopropanes

KW - Chiral auxiliaries

KW - Kulinkovich-de Meijere reaction

KW - Organotitanium chemistry

KW - Polonovski reaction

U2 - 10.1016/j.tetlet.2011.03.026

DO - 10.1016/j.tetlet.2011.03.026

M3 - Article

AN - SCOPUS:79953680225

SN - 0040-4039

VL - 52

SP - 2501

EP - 2504

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Tactics for the asymmetric preparation of 2-azabicyclo[3.1.0]hexane and 2-azabicyclo[4.1.0]heptane scaffolds

Abstract

Keywords

Access to Document

Fingerprint

Cite this