Aromatic spiroketal bisphosphine ligands: Palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts

Xiaoming Wang; Fanye Meng; Yan Wang; Zhaobin Han; Yong Jun Chen; Li Liu; Zheng Wang; Kuiling Ding

doi:10.1002/anie.201204925

Aromatic spiroketal bisphosphine ligands: Palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts

Xiaoming Wang, Fanye Meng, Yan Wang, Zhaobin Han, Yong Jun Chen, Li Liu, Zheng Wang, Kuiling Ding

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

203 Scopus citations

Abstract

Showing a backbone: The spiroketal backbone of the bis(phosphine) ligand 1 led to good regio- and enantioselectivity in the palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts with aromatic amines. The methodology provides a facile and efficient synthesis of precursors for optically active β-lactam derivatives, including the cholesterol drug Ezetimibe.

Original language	English
Pages (from-to)	9276-9282
Number of pages	7
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	37
DOIs	https://doi.org/10.1002/anie.201204925
State	Published - 10 Sep 2012
Externally published	Yes

Keywords

asymmetric catalysis
lactams
palladium
phosphane ligands
spiro compounds

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title = "Aromatic spiroketal bisphosphine ligands: Palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts",

abstract = "Showing a backbone: The spiroketal backbone of the bis(phosphine) ligand 1 led to good regio- and enantioselectivity in the palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts with aromatic amines. The methodology provides a facile and efficient synthesis of precursors for optically active β-lactam derivatives, including the cholesterol drug Ezetimibe.",

keywords = "asymmetric catalysis, lactams, palladium, phosphane ligands, spiro compounds",

author = "Xiaoming Wang and Fanye Meng and Yan Wang and Zhaobin Han and Chen, \{Yong Jun\} and Li Liu and Zheng Wang and Kuiling Ding",

year = "2012",

month = sep,

day = "10",

doi = "10.1002/anie.201204925",

language = "English",

volume = "51",

pages = "9276--9282",

journal = "Angewandte Chemie - International Edition",

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T1 - Aromatic spiroketal bisphosphine ligands

T2 - Palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts

AU - Wang, Xiaoming

AU - Meng, Fanye

AU - Wang, Yan

AU - Han, Zhaobin

AU - Chen, Yong Jun

AU - Liu, Li

AU - Wang, Zheng

AU - Ding, Kuiling

PY - 2012/9/10

Y1 - 2012/9/10

N2 - Showing a backbone: The spiroketal backbone of the bis(phosphine) ligand 1 led to good regio- and enantioselectivity in the palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts with aromatic amines. The methodology provides a facile and efficient synthesis of precursors for optically active β-lactam derivatives, including the cholesterol drug Ezetimibe.

AB - Showing a backbone: The spiroketal backbone of the bis(phosphine) ligand 1 led to good regio- and enantioselectivity in the palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts with aromatic amines. The methodology provides a facile and efficient synthesis of precursors for optically active β-lactam derivatives, including the cholesterol drug Ezetimibe.

KW - asymmetric catalysis

KW - lactams

KW - palladium

KW - phosphane ligands

KW - spiro compounds

UR - https://www.scopus.com/pages/publications/84865838724

U2 - 10.1002/anie.201204925

DO - 10.1002/anie.201204925

M3 - Article

AN - SCOPUS:84865838724

SN - 1433-7851

VL - 51

SP - 9276

EP - 9282

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 37

ER -

Aromatic spiroketal bisphosphine ligands: Palladium-catalyzed asymmetric allylic amination of racemic Morita-Baylis-Hillman adducts

Abstract

Keywords

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