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Bismuth‐Mediated Diastereoselective Allylation Reaction of Carbonyl Compounds with Cyclic Allylic Halides or Cinnamyl Halide
Author(s) -
Liu XuanYu,
Cheng BuQing,
Guo YiCong,
Chu XueQiang,
Li YongXin,
Loh TeckPeng,
Shen ZhiLiang
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801297
Subject(s) - chemistry , halide , allylic rearrangement , bismuth , bromide , allyl bromide , substituent , substrate (aquarium) , organic chemistry , cinnamyl alcohol , diselenide , medicinal chemistry , catalysis , cinnamaldehyde , selenium , oceanography , geology
An efficient diastereoselective allylation of various carbonyl compounds with cyclic allylic halides by using commercially available bismuth powder in the presence of LiI was developed. Among all the metals screened, bismuth was found to be the best mediator for the transformation. The reactions involving various cyclic allylic halides proceeded smoothly at room temperature to produce the desired homoallylic alcohols in good to excellent yields with high diastereoselectivities (>99:1 dr). Reversed diastereoselectivity was obtained when carbonyl substrate (e. g., 2‐pyridinecarboxaldehyde, glyoxylic acid) containing chelating substituent was used in the allylation reaction. In addition, the reactions involving acyclic ( E )‐cinnamyl bromide as substrate worked equally well with high diastereocontrol.