Hexahydropyrrolo [2,3-b]indoles: A new class of structurally rigid tricyclic skeleton for oxazaborolidine-catalyzed asymmetric borane reduction

Jian Xiao; Zhen Zhou Wong; Yun Peng Lu; Teck Peng Loh

doi:10.1002/adsc.200900908

Hexahydropyrrolo [2,3-b]indoles: A new class of structurally rigid tricyclic skeleton for oxazaborolidine-catalyzed asymmetric borane reduction

Jian Xiao, Zhen Zhou Wong, Yun Peng Lu, Teck Peng Loh

Nanyang Technological University

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

15 Citations (Scopus)

Abstract

A new class of structurally rigid tricyclic chiral ligands based on the hexahydropyrrolo [2,3b]indole skeleton has been rationally designed and the catalytic abilities in asymmetric catalysis have been shown in the enantioselective borane reduction of prochiral ketones to afford the chiral alcohols in excellent yields and high enantioselectivities (up to 97% ee).

Original language	English
Pages (from-to)	1107-1112
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	352
Issue number	7
DOIs	https://doi.org/10.1002/adsc.200900908
Publication status	Published - May 3 2010
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
Organic Chemistry

Keywords

Asymmetric catalysis
Chiral skeleton
DFT calculations
Hexahydropyrrolo[2-3- b]indoles
Ketone reduction
Ligand design

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10.1002/adsc.200900908

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title = "Hexahydropyrrolo [2,3-b]indoles: A new class of structurally rigid tricyclic skeleton for oxazaborolidine-catalyzed asymmetric borane reduction",

abstract = "A new class of structurally rigid tricyclic chiral ligands based on the hexahydropyrrolo [2,3b]indole skeleton has been rationally designed and the catalytic abilities in asymmetric catalysis have been shown in the enantioselective borane reduction of prochiral ketones to afford the chiral alcohols in excellent yields and high enantioselectivities (up to 97% ee).",

keywords = "Asymmetric catalysis, Chiral skeleton, DFT calculations, Hexahydropyrrolo[2-3- b]indoles, Ketone reduction, Ligand design",

author = "Jian Xiao and Wong, {Zhen Zhou} and Lu, {Yun Peng} and Loh, {Teck Peng}",

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doi = "10.1002/adsc.200900908",

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journal = "Advanced Synthesis and Catalysis",

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T2 - A new class of structurally rigid tricyclic skeleton for oxazaborolidine-catalyzed asymmetric borane reduction

AU - Xiao, Jian

AU - Wong, Zhen Zhou

AU - Lu, Yun Peng

AU - Loh, Teck Peng

PY - 2010/5/3

Y1 - 2010/5/3

N2 - A new class of structurally rigid tricyclic chiral ligands based on the hexahydropyrrolo [2,3b]indole skeleton has been rationally designed and the catalytic abilities in asymmetric catalysis have been shown in the enantioselective borane reduction of prochiral ketones to afford the chiral alcohols in excellent yields and high enantioselectivities (up to 97% ee).

AB - A new class of structurally rigid tricyclic chiral ligands based on the hexahydropyrrolo [2,3b]indole skeleton has been rationally designed and the catalytic abilities in asymmetric catalysis have been shown in the enantioselective borane reduction of prochiral ketones to afford the chiral alcohols in excellent yields and high enantioselectivities (up to 97% ee).

KW - Asymmetric catalysis

KW - Chiral skeleton

KW - DFT calculations

KW - Hexahydropyrrolo[2-3- b]indoles

KW - Ketone reduction

KW - Ligand design

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DO - 10.1002/adsc.200900908

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JF - Advanced Synthesis and Catalysis

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ER -

Hexahydropyrrolo [2,3-b]indoles: A new class of structurally rigid tricyclic skeleton for oxazaborolidine-catalyzed asymmetric borane reduction

Abstract

ASJC Scopus Subject Areas

Keywords

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