Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their insitu site-, diastereo-, and enantioselective additions to aldehydes and ketones

Fanke Meng; Hwanjong Jang; Byunghyuck Jung; Amir H. Hoveyda

doi:10.1002/anie.201301018

Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their insitu site-, diastereo-, and enantioselective additions to aldehydes and ketones

Fanke Meng, Hwanjong Jang, Byunghyuck Jung, Amir H. Hoveyda

Department of Physics and Chemistry

Boston College

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

171 Scopus citations

Abstract

Sustainable, efficient, selective: A three-component, single-vessel Cu-catalyzed method for chemo-, diastereo-, and enantioselective conversion of B₂(pin)₂, monosubstituted allenes, and aldehydes or ketones to 2-B(pin)-substituted homoallylic alkoxides is described. Subsequent functionalization delivers valuable products in up to >98:2 d.r. and 97:3 e.r. (see scheme).

Original language	English
Pages (from-to)	5046-5051
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	19
DOIs	https://doi.org/10.1002/anie.201301018
State	Published - 3 May 2013

Keywords

aldol products
allylations
copper
enantioselective catalysis
vinylborons

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10.1002/anie.201301018

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title = "Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their insitu site-, diastereo-, and enantioselective additions to aldehydes and ketones",

abstract = "Sustainable, efficient, selective: A three-component, single-vessel Cu-catalyzed method for chemo-, diastereo-, and enantioselective conversion of B2(pin)2, monosubstituted allenes, and aldehydes or ketones to 2-B(pin)-substituted homoallylic alkoxides is described. Subsequent functionalization delivers valuable products in up to >98:2 d.r. and 97:3 e.r. (see scheme).",

keywords = "aldol products, allylations, copper, enantioselective catalysis, vinylborons",

author = "Fanke Meng and Hwanjong Jang and Byunghyuck Jung and Hoveyda, {Amir H.}",

year = "2013",

month = may,

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doi = "10.1002/anie.201301018",

language = "English",

volume = "52",

pages = "5046--5051",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

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}

Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their insitu site-, diastereo-, and enantioselective additions to aldehydes and ketones. / Meng, Fanke; Jang, Hwanjong; Jung, Byunghyuck et al.
In: Angewandte Chemie - International Edition, Vol. 52, No. 19, 03.05.2013, p. 5046-5051.

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

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T1 - Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their insitu site-, diastereo-, and enantioselective additions to aldehydes and ketones

AU - Meng, Fanke

AU - Jang, Hwanjong

AU - Jung, Byunghyuck

AU - Hoveyda, Amir H.

PY - 2013/5/3

Y1 - 2013/5/3

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AB - Sustainable, efficient, selective: A three-component, single-vessel Cu-catalyzed method for chemo-, diastereo-, and enantioselective conversion of B2(pin)2, monosubstituted allenes, and aldehydes or ketones to 2-B(pin)-substituted homoallylic alkoxides is described. Subsequent functionalization delivers valuable products in up to >98:2 d.r. and 97:3 e.r. (see scheme).

KW - aldol products

KW - allylations

KW - copper

KW - enantioselective catalysis

KW - vinylborons

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JO - Angewandte Chemie - International Edition

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ER -

Cu-catalyzed chemoselective preparation of 2-(pinacolato)boron-substituted allylcopper complexes and their insitu site-, diastereo-, and enantioselective additions to aldehydes and ketones

Abstract

Keywords

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