Citation: Wu Zhen, Feng Xue-Xin, Wang Qing-Dong, Liu Xuan-Yu, Rao Weidong, Yang Jin-Ming, Shen Zhi-Liang. An efficient Bi/NH₄I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media[J]. Chinese Chemical Letters, ;2020, 31(2): 391-395. doi: 10.1016/j.cclet.2019.07.030 shu

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

Wu Zhen ^a,b ,
Feng Xue-Xin ^a,b ,
Wang Qing-Dong ^b ,
Liu Xuan-Yu ^a ,
Rao Weidong ^c ,
Yang Jin-Ming ^a,b,*, ,
Shen Zhi-Liang ^a,*,

a.
School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China
b.
School of Pharmacy, Yancheng Teachers University, Yancheng 224007, China
c.
Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

yangjm@yctu.edu.cn

ias_zlshen@njtech.edu.cn

Received Date: 29 May 2019
Revised Date: 11 July 2019
Accepted Date: 11 July 2019
Available Online: 12 July 2019

Figures(6)

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.
- Bismuth,
- Ammonium iodide,
- Water,
- Homoallylic alcohol,
- Diastereoselectivity
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An efficient Bi/NH4I-mediated addition reaction for the highly diastereoselective synthesis of homoallylic alcohols in aqueous media

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通讯作者: 陈斌, bchen63@163.com

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