Pd(II)-Catalyzed Enantioselective Desymmetrization of Polycyclic Cyclohexenediones: Conjugate Addition versus Oxidative Heck

Claire J. C. Lamb; Filipe Vilela; Ai-Lan Lee

doi:10.1021/acs.orglett.9b03293

Pd(II)-Catalyzed Enantioselective Desymmetrization of Polycyclic Cyclohexenediones: Conjugate Addition versus Oxidative Heck

Claire J. C. Lamb, Filipe Vilela, Ai-Lan Lee

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

14 Citations (Scopus)

53 Downloads (Pure)

Abstract

Pd(II)-catalyzed desymmetrization of polycyclic cyclohexenediones has been achieved with high enantio- and diastereoselectivities. Up to five contiguous stereocenters are desymmetrized, while simultaneously, an additional stereocenter is created by the enantioselective conjugate addition. Surprisingly, the conjugate addition products dominate even under typical oxidative Heck conditions, and these observations may provide some insight into the competition between the two related reactions.

Original language	English
Pages (from-to)	8689-8694
Number of pages	6
Journal	Organic Letters
Volume	21
Issue number	21
Early online date	15 Oct 2019
DOIs	https://doi.org/10.1021/acs.orglett.9b03293
Publication status	Published - 1 Nov 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.9b03293

Download pdf
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b03293
Accepted author manuscript, 1.03 MB

Cite this

@article{f4cd4a63d1324c4eb23a991e02266b73,

title = "Pd(II)-Catalyzed Enantioselective Desymmetrization of Polycyclic Cyclohexenediones: Conjugate Addition versus Oxidative Heck",

abstract = "Pd(II)-catalyzed desymmetrization of polycyclic cyclohexenediones has been achieved with high enantio- and diastereoselectivities. Up to five contiguous stereocenters are desymmetrized, while simultaneously, an additional stereocenter is created by the enantioselective conjugate addition. Surprisingly, the conjugate addition products dominate even under typical oxidative Heck conditions, and these observations may provide some insight into the competition between the two related reactions.",

author = "Lamb, {Claire J. C.} and Filipe Vilela and Ai-Lan Lee",

year = "2019",

month = nov,

day = "1",

doi = "10.1021/acs.orglett.9b03293",

language = "English",

volume = "21",

pages = "8689--8694",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Pd(II)-Catalyzed Enantioselective Desymmetrization of Polycyclic Cyclohexenediones

T2 - Conjugate Addition versus Oxidative Heck

AU - Lamb, Claire J. C.

AU - Vilela, Filipe

AU - Lee, Ai-Lan

PY - 2019/11/1

Y1 - 2019/11/1

N2 - Pd(II)-catalyzed desymmetrization of polycyclic cyclohexenediones has been achieved with high enantio- and diastereoselectivities. Up to five contiguous stereocenters are desymmetrized, while simultaneously, an additional stereocenter is created by the enantioselective conjugate addition. Surprisingly, the conjugate addition products dominate even under typical oxidative Heck conditions, and these observations may provide some insight into the competition between the two related reactions.

AB - Pd(II)-catalyzed desymmetrization of polycyclic cyclohexenediones has been achieved with high enantio- and diastereoselectivities. Up to five contiguous stereocenters are desymmetrized, while simultaneously, an additional stereocenter is created by the enantioselective conjugate addition. Surprisingly, the conjugate addition products dominate even under typical oxidative Heck conditions, and these observations may provide some insight into the competition between the two related reactions.

UR - http://www.scopus.com/inward/record.url?scp=85073877205&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b03293

DO - 10.1021/acs.orglett.9b03293

M3 - Article

C2 - 31613102

SN - 1523-7060

VL - 21

SP - 8689

EP - 8694

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Pd(II)-Catalyzed Enantioselective Desymmetrization of Polycyclic Cyclohexenediones: Conjugate Addition versus Oxidative Heck

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint