Highly diastereoselective and enantioselective formal [4 + 3] cycloaddition of donor-acceptor cyclobutanes with nitrones

Jiang Lin Hu; Lijia Wang; Hao Xu; Zuowei Xie; Yong Tang

doi:10.1021/acs.orglett.5b01077

Highly diastereoselective and enantioselective formal [4 + 3] cycloaddition of donor-acceptor cyclobutanes with nitrones

Jiang Lin Hu
, Lijia Wang
, Hao Xu
, Zuowei Xie^*
, Yong Tang

^*Corresponding author for this work

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

80 Scopus citations

Abstract

The first highly diastereoselective and enantioselective catalytic formal [4 + 3] cycloaddition of 1,1-cyclobutane diester with nitrone has been developed. Sterically hindered chiral SaBOX/Cu(II) complex promotes the reaction efficiently with a broad substrate scope, producing a range of multifunctionalized optically active 1,2-oxazepanes with excellent stereocontrol (up to >99/1 dr and 97% ee).

Original language	English
Pages (from-to)	2680-2683
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.5b01077
State	Published - 5 Jun 2015
Externally published	Yes

Access to Document

10.1021/acs.orglett.5b01077

Cite this

@article{6ce7167aaddb469390106aeb0e8a90ad,

title = "Highly diastereoselective and enantioselective formal [4 + 3] cycloaddition of donor-acceptor cyclobutanes with nitrones",

abstract = "The first highly diastereoselective and enantioselective catalytic formal [4 + 3] cycloaddition of 1,1-cyclobutane diester with nitrone has been developed. Sterically hindered chiral SaBOX/Cu(II) complex promotes the reaction efficiently with a broad substrate scope, producing a range of multifunctionalized optically active 1,2-oxazepanes with excellent stereocontrol (up to >99/1 dr and 97\% ee).",

author = "Hu, \{Jiang Lin\} and Lijia Wang and Hao Xu and Zuowei Xie and Yong Tang",

note = "Publisher Copyright: {\textcopyright} 2015 American Chemical Society.",

year = "2015",

month = jun,

day = "5",

doi = "10.1021/acs.orglett.5b01077",

language = "英语",

volume = "17",

pages = "2680--2683",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "11",

}

TY - JOUR

T1 - Highly diastereoselective and enantioselective formal [4 + 3] cycloaddition of donor-acceptor cyclobutanes with nitrones

AU - Hu, Jiang Lin

AU - Wang, Lijia

AU - Xu, Hao

AU - Xie, Zuowei

AU - Tang, Yong

PY - 2015/6/5

Y1 - 2015/6/5

N2 - The first highly diastereoselective and enantioselective catalytic formal [4 + 3] cycloaddition of 1,1-cyclobutane diester with nitrone has been developed. Sterically hindered chiral SaBOX/Cu(II) complex promotes the reaction efficiently with a broad substrate scope, producing a range of multifunctionalized optically active 1,2-oxazepanes with excellent stereocontrol (up to >99/1 dr and 97% ee).

AB - The first highly diastereoselective and enantioselective catalytic formal [4 + 3] cycloaddition of 1,1-cyclobutane diester with nitrone has been developed. Sterically hindered chiral SaBOX/Cu(II) complex promotes the reaction efficiently with a broad substrate scope, producing a range of multifunctionalized optically active 1,2-oxazepanes with excellent stereocontrol (up to >99/1 dr and 97% ee).

UR - https://www.scopus.com/pages/publications/84930960129

U2 - 10.1021/acs.orglett.5b01077

DO - 10.1021/acs.orglett.5b01077

M3 - 文章

C2 - 25974724

AN - SCOPUS:84930960129

SN - 1523-7060

VL - 17

SP - 2680

EP - 2683

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Highly diastereoselective and enantioselective formal [4 + 3] cycloaddition of donor-acceptor cyclobutanes with nitrones

Abstract

Access to Document

Other files and links

Fingerprint

Cite this