The stereochemistry of 1,3-dipolar cycloaddition of internally H-bonded chiral methylenenitrones

Shaikh A. Ali; Muhammad Z.N. Iman

doi:10.1016/j.tet.2007.06.067

The stereochemistry of 1,3-dipolar cycloaddition of internally H-bonded chiral methylenenitrones

Shaikh A. Ali^*, Muhammad Z.N. Iman

^*Corresponding author for this work

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

19 Scopus citations

Abstract

A study of diastereoselectivity in the cycloaddition reactions of a series of mono- and disubstituted alkenes with two chiral, internally H-bonded methylenenitrones has been carried out. The high degree of stereochemical control in the presence of anhydrous magnesium bromide has been explained in terms of a metal chelated transition state. Intramolecular cycloaddition involving a methylenenitrone containing an alkene moiety linked to a nitrogen gave a stereoselective addition product.

Original language	English
Pages (from-to)	9134-9145
Number of pages	12
Journal	Tetrahedron
Volume	63
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2007.06.067
State	Published - 10 Sep 2007

Keywords

Asymmetric induction
Diastereoselection
Lewis acid catalyst
Nitrone cycloaddition

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2007.06.067

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title = "The stereochemistry of 1,3-dipolar cycloaddition of internally H-bonded chiral methylenenitrones",

abstract = "A study of diastereoselectivity in the cycloaddition reactions of a series of mono- and disubstituted alkenes with two chiral, internally H-bonded methylenenitrones has been carried out. The high degree of stereochemical control in the presence of anhydrous magnesium bromide has been explained in terms of a metal chelated transition state. Intramolecular cycloaddition involving a methylenenitrone containing an alkene moiety linked to a nitrogen gave a stereoselective addition product.",

keywords = "Asymmetric induction, Diastereoselection, Lewis acid catalyst, Nitrone cycloaddition",

author = "Ali, \{Shaikh A.\} and Iman, \{Muhammad Z.N.\}",

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T1 - The stereochemistry of 1,3-dipolar cycloaddition of internally H-bonded chiral methylenenitrones

AU - Ali, Shaikh A.

AU - Iman, Muhammad Z.N.

PY - 2007/9/10

Y1 - 2007/9/10

N2 - A study of diastereoselectivity in the cycloaddition reactions of a series of mono- and disubstituted alkenes with two chiral, internally H-bonded methylenenitrones has been carried out. The high degree of stereochemical control in the presence of anhydrous magnesium bromide has been explained in terms of a metal chelated transition state. Intramolecular cycloaddition involving a methylenenitrone containing an alkene moiety linked to a nitrogen gave a stereoselective addition product.

AB - A study of diastereoselectivity in the cycloaddition reactions of a series of mono- and disubstituted alkenes with two chiral, internally H-bonded methylenenitrones has been carried out. The high degree of stereochemical control in the presence of anhydrous magnesium bromide has been explained in terms of a metal chelated transition state. Intramolecular cycloaddition involving a methylenenitrone containing an alkene moiety linked to a nitrogen gave a stereoselective addition product.

KW - Asymmetric induction

KW - Diastereoselection

KW - Lewis acid catalyst

KW - Nitrone cycloaddition

UR - https://www.scopus.com/pages/publications/34547400063

U2 - 10.1016/j.tet.2007.06.067

DO - 10.1016/j.tet.2007.06.067

M3 - Article

AN - SCOPUS:34547400063

SN - 0040-4020

VL - 63

SP - 9134

EP - 9145

JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

The stereochemistry of 1,3-dipolar cycloaddition of internally H-bonded chiral methylenenitrones

Abstract

Keywords

ASJC Scopus subject areas

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