Enantioselective synthesis of 2,6-cis-disubstituted tetrahydropyrans via a tandem catalytic asymmetric hydrogenation/oxa-Michael cyclization: An efficient approach to (-)-centrolobine

Jian Hua Xie; Lu Chuan Guo; Xiao Hui Yang; Li Xin Wang; Qi Lin Zhou

doi:10.1021/ol3020144

Enantioselective synthesis of 2,6-cis-disubstituted tetrahydropyrans via a tandem catalytic asymmetric hydrogenation/oxa-Michael cyclization: An efficient approach to (-)-centrolobine

Jian Hua Xie^*, Lu Chuan Guo, Xiao Hui Yang, Li Xin Wang, Qi Lin Zhou

^*Corresponding author for this work

Nankai University

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

43 Citations (Scopus)

Abstract

A highly efficient one-pot process via a tandem reaction of catalytic asymmetric hydrogenation and oxa-Michael cyclization for the synthesis of 2,6-cis-disubstituted tetrahydropyrans has been developed (ee up to 99.9%, cis/trans-selectivity up to 99:1). This method provides a concise route to (-)-centrolobine (68.8% yield, three steps).

Original language	English
Pages (from-to)	4758-4761
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	18
DOIs	https://doi.org/10.1021/ol3020144
Publication status	Published - 21 Sept 2012
Externally published	Yes

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10.1021/ol3020144

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title = "Enantioselective synthesis of 2,6-cis-disubstituted tetrahydropyrans via a tandem catalytic asymmetric hydrogenation/oxa-Michael cyclization: An efficient approach to (-)-centrolobine",

abstract = "A highly efficient one-pot process via a tandem reaction of catalytic asymmetric hydrogenation and oxa-Michael cyclization for the synthesis of 2,6-cis-disubstituted tetrahydropyrans has been developed (ee up to 99.9%, cis/trans-selectivity up to 99:1). This method provides a concise route to (-)-centrolobine (68.8% yield, three steps).",

author = "Xie, {Jian Hua} and Guo, {Lu Chuan} and Yang, {Xiao Hui} and Wang, {Li Xin} and Zhou, {Qi Lin}",

year = "2012",

month = sep,

day = "21",

doi = "10.1021/ol3020144",

language = "English",

volume = "14",

pages = "4758--4761",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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Enantioselective synthesis of 2,6-cis-disubstituted tetrahydropyrans via a tandem catalytic asymmetric hydrogenation/oxa-Michael cyclization: An efficient approach to (-)-centrolobine. / Xie, Jian Hua; Guo, Lu Chuan; Yang, Xiao Hui et al.
In: Organic Letters, Vol. 14, No. 18, 21.09.2012, p. 4758-4761.

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

TY - JOUR

T1 - Enantioselective synthesis of 2,6-cis-disubstituted tetrahydropyrans via a tandem catalytic asymmetric hydrogenation/oxa-Michael cyclization

T2 - An efficient approach to (-)-centrolobine

AU - Xie, Jian Hua

AU - Guo, Lu Chuan

AU - Yang, Xiao Hui

AU - Wang, Li Xin

AU - Zhou, Qi Lin

PY - 2012/9/21

Y1 - 2012/9/21

N2 - A highly efficient one-pot process via a tandem reaction of catalytic asymmetric hydrogenation and oxa-Michael cyclization for the synthesis of 2,6-cis-disubstituted tetrahydropyrans has been developed (ee up to 99.9%, cis/trans-selectivity up to 99:1). This method provides a concise route to (-)-centrolobine (68.8% yield, three steps).

AB - A highly efficient one-pot process via a tandem reaction of catalytic asymmetric hydrogenation and oxa-Michael cyclization for the synthesis of 2,6-cis-disubstituted tetrahydropyrans has been developed (ee up to 99.9%, cis/trans-selectivity up to 99:1). This method provides a concise route to (-)-centrolobine (68.8% yield, three steps).

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SN - 1523-7060

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EP - 4761

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -

Enantioselective synthesis of 2,6-cis-disubstituted tetrahydropyrans via a tandem catalytic asymmetric hydrogenation/oxa-Michael cyclization: An efficient approach to (-)-centrolobine

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