Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

Xiao Hui Yang; Hai Tao Yue; Na Yu; Yi Pan Li; Jian Hua Xie; Qi Lin Zhou

doi:10.1039/c6sc04609f

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

Xiao Hui Yang
, Hai Tao Yue
, Na Yu
, Yi Pan Li
, Jian Hua Xie^*
, Qi Lin Zhou

^*Corresponding author for this work

Nankai University
State Key Laboratory
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)

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

42 Citations (Scopus)

Abstract

We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (−)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

Original language	English
Pages (from-to)	1811-1814
Number of pages	4
Journal	Chemical Science
Volume	8
Issue number	3
DOIs	https://doi.org/10.1039/c6sc04609f
Publication status	Published - 2017
Externally published	Yes

Access to Document

10.1039/c6sc04609f

Cite this

@article{1de157fbd083426585cca413ea53cd86,

title = "Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols",

abstract = "We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95\%) with a high enantioselectivity (up to 95\% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (−)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.",

author = "Yang, \{Xiao Hui\} and Yue, \{Hai Tao\} and Na Yu and Li, \{Yi Pan\} and Xie, \{Jian Hua\} and Zhou, \{Qi Lin\}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2017",

doi = "10.1039/c6sc04609f",

language = "English",

volume = "8",

pages = "1811--1814",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "3",

}

TY - JOUR

T1 - Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

AU - Yang, Xiao Hui

AU - Yue, Hai Tao

AU - Yu, Na

AU - Li, Yi Pan

AU - Xie, Jian Hua

AU - Zhou, Qi Lin

PY - 2017

Y1 - 2017

N2 - We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (−)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

AB - We report a protocol for the highly efficient iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones via dynamic kinetic resolution. Using Ir-SpiroPAP (R)-1d as a catalyst, a wide range of chiral diols were prepared in a high yield (80-95%) with a high enantioselectivity (up to 95% ee) under mild reaction conditions. This protocol was used for enantioselective syntheses of (−)-preclamol and a chiral 2,5-disubstituted tetrahydropyran.

UR - https://www.scopus.com/pages/publications/85014100490

U2 - 10.1039/c6sc04609f

DO - 10.1039/c6sc04609f

M3 - Article

AN - SCOPUS:85014100490

SN - 2041-6520

VL - 8

SP - 1811

EP - 1814

JO - Chemical Science

JF - Chemical Science

IS - 3

ER -

Iridium-catalyzed asymmetric hydrogenation of racemic α-substituted lactones to chiral diols

Abstract

Access to Document

Other files and links

Fingerprint

Cite this