Reductive Carbocyclization of Homoallylic Alcohols to syn-Cyclobutanes by a Boron-Catalyzed Dual Ring-Closing Pathway

Chinmoy Kumar Hazra; Jinhoon Jeong; Hyunjoong Kim; Mu Hyun Baik; Sehoon Park; Sukbok Chang

doi:10.1002/anie.201713285

Reductive Carbocyclization of Homoallylic Alcohols to syn-Cyclobutanes by a Boron-Catalyzed Dual Ring-Closing Pathway

Chinmoy Kumar Hazra, Jinhoon Jeong, Hyunjoong Kim, Mu Hyun Baik^*, Sehoon Park, Sukbok Chang

^*Corresponding author for this work

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

27 Scopus citations

Abstract

The organoborane-catalyzed reductive carbocyclization of homoallylic alcohols has been developed by using hydrosilanes as reducing reagents to provide a range of 1,2-disubstituted arylcyclobutanes. The reaction proceeds in a cis-selective manner with high efficiency under mild conditions. Mechanistic studies, including deuterium scrambling and Hammett studies, and DFT calculations, suggest a dual ring-closing pathway.

Original language	English
Pages (from-to)	2692-2696
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	10
DOIs	https://doi.org/10.1002/anie.201713285
State	Published - 1 Mar 2018
Externally published	Yes

Keywords

carbocyclization
cyclobutanes
homoallylic alcohols
neighboring-group effects
ring-closing

Access to Document

10.1002/anie.201713285

Cite this

@article{d2f61976e2184ad3a1842e807c53f017,

title = "Reductive Carbocyclization of Homoallylic Alcohols to syn-Cyclobutanes by a Boron-Catalyzed Dual Ring-Closing Pathway",

abstract = "The organoborane-catalyzed reductive carbocyclization of homoallylic alcohols has been developed by using hydrosilanes as reducing reagents to provide a range of 1,2-disubstituted arylcyclobutanes. The reaction proceeds in a cis-selective manner with high efficiency under mild conditions. Mechanistic studies, including deuterium scrambling and Hammett studies, and DFT calculations, suggest a dual ring-closing pathway.",

keywords = "carbocyclization, cyclobutanes, homoallylic alcohols, neighboring-group effects, ring-closing",

author = "Hazra, {Chinmoy Kumar} and Jinhoon Jeong and Hyunjoong Kim and Baik, {Mu Hyun} and Sehoon Park and Sukbok Chang",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = mar,

day = "1",

doi = "10.1002/anie.201713285",

language = "英语",

volume = "57",

pages = "2692--2696",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "10",

}

TY - JOUR

T1 - Reductive Carbocyclization of Homoallylic Alcohols to syn-Cyclobutanes by a Boron-Catalyzed Dual Ring-Closing Pathway

AU - Hazra, Chinmoy Kumar

AU - Jeong, Jinhoon

AU - Kim, Hyunjoong

AU - Baik, Mu Hyun

AU - Park, Sehoon

AU - Chang, Sukbok

PY - 2018/3/1

Y1 - 2018/3/1

N2 - The organoborane-catalyzed reductive carbocyclization of homoallylic alcohols has been developed by using hydrosilanes as reducing reagents to provide a range of 1,2-disubstituted arylcyclobutanes. The reaction proceeds in a cis-selective manner with high efficiency under mild conditions. Mechanistic studies, including deuterium scrambling and Hammett studies, and DFT calculations, suggest a dual ring-closing pathway.

AB - The organoborane-catalyzed reductive carbocyclization of homoallylic alcohols has been developed by using hydrosilanes as reducing reagents to provide a range of 1,2-disubstituted arylcyclobutanes. The reaction proceeds in a cis-selective manner with high efficiency under mild conditions. Mechanistic studies, including deuterium scrambling and Hammett studies, and DFT calculations, suggest a dual ring-closing pathway.

KW - carbocyclization

KW - cyclobutanes

KW - homoallylic alcohols

KW - neighboring-group effects

KW - ring-closing

UR - http://www.scopus.com/inward/record.url?scp=85041598605&partnerID=8YFLogxK

U2 - 10.1002/anie.201713285

DO - 10.1002/anie.201713285

M3 - 文章

C2 - 29327487

AN - SCOPUS:85041598605

SN - 1433-7851

VL - 57

SP - 2692

EP - 2696

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 10

ER -

Reductive Carbocyclization of Homoallylic Alcohols to syn-Cyclobutanes by a Boron-Catalyzed Dual Ring-Closing Pathway

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this