Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides

Kirill Tchabanenko; Colleen Sloan; Yves-Mael Bunetel; Philip Mullen

doi:10.1039/c2ob07007c

Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides

Kirill Tchabanenko, Colleen Sloan, Yves-Mael Bunetel, Philip Mullen

School of Chemistry and Chemical Engineering

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

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Abstract

Chiral enamides5f-i were found to react with pyrylium ylides to give cycloadducts 6d-i in good yields with an excellent level of stereoselectivity. The chiral auxiliary was successfully removed on hydrogenolysis of compound 6f in continuous flow (H-Cube) resulting in the first asymmetric synthesis of complex amine 8.

Original language	English
Pages (from-to)	4215-4219
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	21
Early online date	19 Mar 2012
DOIs	https://doi.org/10.1039/c2ob07007c
Publication status	Published - 2012

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Biochemistry

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10.1039/c2ob07007c

Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral
© The Royal Society of Chemistry 2012 This is an open access Creative Commons Attribution-NonCommercial License (https://creativecommons.org/licenses/by-nc/4.0/), which permits use, distribution and reproduction for non-commercial purposes, provided the author and source are cited.
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title = "Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides",

abstract = "Chiral enamides5f-i were found to react with pyrylium ylides to give cycloadducts 6d-i in good yields with an excellent level of stereoselectivity. The chiral auxiliary was successfully removed on hydrogenolysis of compound 6f in continuous flow (H-Cube) resulting in the first asymmetric synthesis of complex amine 8. ",

author = "Kirill Tchabanenko and Colleen Sloan and Yves-Mael Bunetel and Philip Mullen",

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AU - Tchabanenko, Kirill

AU - Sloan, Colleen

AU - Bunetel, Yves-Mael

AU - Mullen, Philip

PY - 2012

Y1 - 2012

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AB - Chiral enamides5f-i were found to react with pyrylium ylides to give cycloadducts 6d-i in good yields with an excellent level of stereoselectivity. The chiral auxiliary was successfully removed on hydrogenolysis of compound 6f in continuous flow (H-Cube) resulting in the first asymmetric synthesis of complex amine 8.

U2 - 10.1039/c2ob07007c

DO - 10.1039/c2ob07007c

M3 - Article

SN - 1477-0520

VL - 10

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EP - 4219

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 21

ER -

Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides

Abstract

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