An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

Zhen Wu; Xue Xin Feng; Qing Dong Wang; Xuan Yu Liu; Weidong Rao; Jin Ming Yang; Zhi Liang Shen

doi:10.1016/j.cclet.2019.07.030

An efficient Bi/NH₄I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

Zhen Wu, Xue Xin Feng, Qing Dong Wang, Xuan Yu Liu, Weidong Rao, Jin Ming Yang, Zhi Liang Shen

School of Chemistry and Moleculai Engineering

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

4 Scopus citations

Abstract

An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed. The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities (>99:1 syn:anti). Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate.

Original language	English
Pages (from-to)	391-395
Number of pages	5
Journal	Chinese Chemical Letters
Volume	31
Issue number	2
DOIs	https://doi.org/10.1016/j.cclet.2019.07.030
State	Published - Feb 2020

Keywords

Ammonium iodide
Bismuth
Diastereoselectivity
Homoallylic alcohol
Water

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10.1016/j.cclet.2019.07.030

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title = "An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media",

abstract = "An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed. The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities (>99:1 syn:anti). Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate.",

keywords = "Ammonium iodide, Bismuth, Diastereoselectivity, Homoallylic alcohol, Water",

author = "Zhen Wu and Feng, {Xue Xin} and Wang, {Qing Dong} and Liu, {Xuan Yu} and Weidong Rao and Yang, {Jin Ming} and Shen, {Zhi Liang}",

note = "Publisher Copyright: {\textcopyright} 2020 The Author",

year = "2020",

month = feb,

doi = "10.1016/j.cclet.2019.07.030",

language = "英语",

volume = "31",

pages = "391--395",

journal = "Chinese Chemical Letters",

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TY - JOUR

T1 - An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

AU - Wu, Zhen

AU - Feng, Xue Xin

AU - Wang, Qing Dong

AU - Liu, Xuan Yu

AU - Rao, Weidong

AU - Yang, Jin Ming

AU - Shen, Zhi Liang

PY - 2020/2

Y1 - 2020/2

N2 - An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed. The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities (>99:1 syn:anti). Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate.

AB - An efficient water-based bismuth-mediated addition reaction of carbonyl compound with cyclic allylic halide was developed. The reactions proceeded smoothly in aqueous DMF in the presence of ammonium iodide to afford the corresponding syn-homoallylic alcohols in moderate to good yields with excellent diastereoselectivities (>99:1 syn:anti). Reversal of product diastereoselectivity was observed when heteroaryl aldehyde possessing an adjacent chelating nitrogen atom was employed as substrate.

KW - Ammonium iodide

KW - Bismuth

KW - Diastereoselectivity

KW - Homoallylic alcohol

KW - Water

UR - http://www.scopus.com/inward/record.url?scp=85070795840&partnerID=8YFLogxK

U2 - 10.1016/j.cclet.2019.07.030

DO - 10.1016/j.cclet.2019.07.030

M3 - 文章

AN - SCOPUS:85070795840

SN - 1001-8417

VL - 31

SP - 391

EP - 395

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 2

ER -

An efficient Bi/NH₄I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

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Keywords

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