Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water

Bo Zhu; Lin Yan; Yuanhang Pan; Richmond Lee; Hongjun Liu; Zhiqiang Han; Kuo-Wei Huang; Choonhong Tan; Zhiyong Jiang

doi:10.1021/jo201096e

Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water

Bo Zhu, Lin Yan, Yuanhang Pan, Richmond Lee, Hongjun Liu, Zhiqiang Han, Kuo-Wei Huang, Choonhong Tan, Zhiyong Jiang

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

33 Scopus citations

Abstract

A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using 18O-labeling experiments. © 2011 American Chemical Society.

Original language	English (US)
Pages (from-to)	6894-6900
Number of pages	7
Journal	The Journal of Organic Chemistry
Volume	76
Issue number	16
DOIs	https://doi.org/10.1021/jo201096e
State	Published - Aug 19 2011

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Financial support from the National Natural Science Foundation of China (21072044 to Z.J.), Excellent Youth Foundation of Henan Scientific Committee (114100510003 to Z.J.), International Cooperation Foundation of Henan Province (104300510062 to Z.J. and C.-H.T.), and ARE Grants (R-143-000-337-112 and R-143-000-342-112 to C.H.T.) is greatly appreciated.

ASJC Scopus subject areas

Organic Chemistry

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title = "Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water",

abstract = "A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using 18O-labeling experiments. {\textcopyright} 2011 American Chemical Society.",

author = "Bo Zhu and Lin Yan and Yuanhang Pan and Richmond Lee and Hongjun Liu and Zhiqiang Han and Kuo-Wei Huang and Choonhong Tan and Zhiyong Jiang",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Financial support from the National Natural Science Foundation of China (21072044 to Z.J.), Excellent Youth Foundation of Henan Scientific Committee (114100510003 to Z.J.), International Cooperation Foundation of Henan Province (104300510062 to Z.J. and C.-H.T.), and ARE Grants (R-143-000-337-112 and R-143-000-342-112 to C.H.T.) is greatly appreciated.",

year = "2011",

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doi = "10.1021/jo201096e",

language = "English (US)",

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pages = "6894--6900",

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T1 - Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water

AU - Zhu, Bo

AU - Yan, Lin

AU - Pan, Yuanhang

AU - Lee, Richmond

AU - Liu, Hongjun

AU - Han, Zhiqiang

AU - Huang, Kuo-Wei

AU - Tan, Choonhong

AU - Jiang, Zhiyong

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: Financial support from the National Natural Science Foundation of China (21072044 to Z.J.), Excellent Youth Foundation of Henan Scientific Committee (114100510003 to Z.J.), International Cooperation Foundation of Henan Province (104300510062 to Z.J. and C.-H.T.), and ARE Grants (R-143-000-337-112 and R-143-000-342-112 to C.H.T.) is greatly appreciated.

PY - 2011/8/19

Y1 - 2011/8/19

N2 - A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using 18O-labeling experiments. © 2011 American Chemical Society.

AB - A Lewis base catalyzed allylic hydroxylation of Morita-Baylis-Hillman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using 18O-labeling experiments. © 2011 American Chemical Society.

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UR - https://pubs.acs.org/doi/10.1021/jo201096e

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DO - 10.1021/jo201096e

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JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 16

ER -

Lewis base catalyzed enantioselective allylic hydroxylation of Morita-Baylis-Hillman carbonates with water

Abstract

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