Photochemical studies on exo-bicyclo[2.1.1]hexyl and bicyclo[3.1.0]hexyl aryl ketones: two approaches for synthesis of enantiomerically enriched cyclopentene derivatives

Guolei Zhao; Chao Yang; Qian Chen; Jing Jin; Xiao Zhang; Liyan Zhao; Wujiong Xia

doi:10.1016/j.tet.2009.10.011

Photochemical studies on exo-bicyclo[2.1.1]hexyl and bicyclo[3.1.0]hexyl aryl ketones: two approaches for synthesis of enantiomerically enriched cyclopentene derivatives

Guolei Zhao
, Chao Yang
, Qian Chen
, Jing Jin
, Xiao Zhang
, Liyan Zhao
, Wujiong Xia^*

^*Corresponding author for this work

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

16 Scopus citations

Abstract

Two approaches for the photochemical synthesis of cyclopentene derivatives through the Norrish type II cleavage reaction were described. Asymmetric studies using ionic chiral auxiliaries afforded enantiomeric excesses of up to 98% at the conversion of 85%. The results were rationalized by single X-ray crystal structures.

Original language	English
Pages (from-to)	9952-9955
Number of pages	4
Journal	Tetrahedron
Volume	65
Issue number	48
DOIs	https://doi.org/10.1016/j.tet.2009.10.011
State	Published - 28 Nov 2009

Keywords

Chiral auxiliary
Cyclopentene
Norrish type II
Photochemical synthesis

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10.1016/j.tet.2009.10.011

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title = "Photochemical studies on exo-bicyclo[2.1.1]hexyl and bicyclo[3.1.0]hexyl aryl ketones: two approaches for synthesis of enantiomerically enriched cyclopentene derivatives",

abstract = "Two approaches for the photochemical synthesis of cyclopentene derivatives through the Norrish type II cleavage reaction were described. Asymmetric studies using ionic chiral auxiliaries afforded enantiomeric excesses of up to 98\% at the conversion of 85\%. The results were rationalized by single X-ray crystal structures.",

keywords = "Chiral auxiliary, Cyclopentene, Norrish type II, Photochemical synthesis",

author = "Guolei Zhao and Chao Yang and Qian Chen and Jing Jin and Xiao Zhang and Liyan Zhao and Wujiong Xia",

year = "2009",

month = nov,

day = "28",

doi = "10.1016/j.tet.2009.10.011",

language = "英语",

volume = "65",

pages = "9952--9955",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "48",

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TY - JOUR

T1 - Photochemical studies on exo-bicyclo[2.1.1]hexyl and bicyclo[3.1.0]hexyl aryl ketones

T2 - two approaches for synthesis of enantiomerically enriched cyclopentene derivatives

AU - Zhao, Guolei

AU - Yang, Chao

AU - Chen, Qian

AU - Jin, Jing

AU - Zhang, Xiao

AU - Zhao, Liyan

AU - Xia, Wujiong

PY - 2009/11/28

Y1 - 2009/11/28

N2 - Two approaches for the photochemical synthesis of cyclopentene derivatives through the Norrish type II cleavage reaction were described. Asymmetric studies using ionic chiral auxiliaries afforded enantiomeric excesses of up to 98% at the conversion of 85%. The results were rationalized by single X-ray crystal structures.

AB - Two approaches for the photochemical synthesis of cyclopentene derivatives through the Norrish type II cleavage reaction were described. Asymmetric studies using ionic chiral auxiliaries afforded enantiomeric excesses of up to 98% at the conversion of 85%. The results were rationalized by single X-ray crystal structures.

KW - Chiral auxiliary

KW - Cyclopentene

KW - Norrish type II

KW - Photochemical synthesis

UR - https://www.scopus.com/pages/publications/70350441370

U2 - 10.1016/j.tet.2009.10.011

DO - 10.1016/j.tet.2009.10.011

M3 - 文章

AN - SCOPUS:70350441370

SN - 0040-4020

VL - 65

SP - 9952

EP - 9955

JO - Tetrahedron

JF - Tetrahedron

IS - 48

ER -

Photochemical studies on exo-bicyclo[2.1.1]hexyl and bicyclo[3.1.0]hexyl aryl ketones: two approaches for synthesis of enantiomerically enriched cyclopentene derivatives

Abstract

Keywords

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