Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration

Yunfei Luo; Steven M. Wales; Stamatis E. Korkis; Iain D. Roy; William Lewis; Hon Wai Lam

doi:10.1002/chem.201801804

Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration

Yunfei Luo
, Steven M. Wales
, Stamatis E. Korkis
, Iain D. Roy
, William Lewis
, Hon Wai Lam^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

14 Citations (Scopus)

Abstract

The enantioselective Cu-catalyzed 1,6-boration of (E,E)-α,β,γ,δ-unsaturated ketones is described, which gives homoallylic boronates with high enantiomeric purity and unexpectedly high Z-selectivity. By changing the solvent, the outcome can be altered to give E-allylic boronates.

Original language	English
Pages (from-to)	8315-8319
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	33
Early online date	17 Apr 2018
DOIs	https://doi.org/10.1002/chem.201801804
Publication status	Published - 12 Jun 2018

Keywords

1,6-addition
asymmetric catalysis
boron
copper
enantioselectivity

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@article{660db41d3eaa47c28a94ec8138fd20ec,

title = "Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration",

abstract = "The enantioselective Cu-catalyzed 1,6-boration of (E,E)-α,β,γ,δ-unsaturated ketones is described, which gives homoallylic boronates with high enantiomeric purity and unexpectedly high Z-selectivity. By changing the solvent, the outcome can be altered to give E-allylic boronates.",

keywords = "1,6-addition, asymmetric catalysis, boron, copper, enantioselectivity",

author = "Yunfei Luo and Wales, \{Steven M.\} and Korkis, \{Stamatis E.\} and Roy, \{Iain D.\} and William Lewis and Lam, \{Hon Wai\}",

year = "2018",

month = jun,

day = "12",

doi = "10.1002/chem.201801804",

language = "English",

volume = "24",

pages = "8315--8319",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley and Sons Inc",

number = "33",

}

TY - JOUR

T1 - Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration

AU - Luo, Yunfei

AU - Wales, Steven M.

AU - Korkis, Stamatis E.

AU - Roy, Iain D.

AU - Lewis, William

AU - Lam, Hon Wai

PY - 2018/6/12

Y1 - 2018/6/12

N2 - The enantioselective Cu-catalyzed 1,6-boration of (E,E)-α,β,γ,δ-unsaturated ketones is described, which gives homoallylic boronates with high enantiomeric purity and unexpectedly high Z-selectivity. By changing the solvent, the outcome can be altered to give E-allylic boronates.

AB - The enantioselective Cu-catalyzed 1,6-boration of (E,E)-α,β,γ,δ-unsaturated ketones is described, which gives homoallylic boronates with high enantiomeric purity and unexpectedly high Z-selectivity. By changing the solvent, the outcome can be altered to give E-allylic boronates.

KW - 1,6-addition

KW - asymmetric catalysis

KW - boron

KW - copper

KW - enantioselectivity

UR - https://www.scopus.com/pages/publications/85047473732

U2 - 10.1002/chem.201801804

DO - 10.1002/chem.201801804

M3 - Article (Academic Journal)

C2 - 29665113

AN - SCOPUS:85047473732

SN - 0947-6539

VL - 24

SP - 8315

EP - 8319

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 33

ER -

Switchable Synthesis of Z-Homoallylic Boronates and E-Allylic Boronates by Enantioselective Copper-Catalyzed 1,6-Boration

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Keywords

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