期刊
TETRAHEDRON
卷 72, 期 44, 页码 6914-6928出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.09.005
关键词
Trialkylborane; Sulfoximine; Rearrangement; Sulfoxide; Sulfone
资金
- Deanship of Scientific Research at King Saud University [RGP-239]
Known reagents that transfer three alkyl groups of a trialkylborane intramolecularly to a single carbon atom lack features to influence stereochemistry. We have investigated four reagents of type LiCCl2X, where X might be amenable to variation. All behaved differently. With X=OR (R=cyclohexyl, menthyl), the reagent decomposed, leading to only low yields of triple migration products. With X=S(O)Ph, a single migration occurred, followed by isomerisation to boron enolate-like species that hydrolysed to alpha-chloroalkyl phenyl sulfoxides or reacted with aldehydes to aldol-like.products. With X=SO2Ph, the major product was the corresponding a,a-dichloroallcyl phenyl sulfone, apparently formed through a redox reaction. With X=S(O)(NMe)Ph, products of three intramolecular alkyl migrations were obtained with unhindered trialkylboranes. Attempts have been made to gain understanding of the sulfoxide process by investigating proportions of aldol-like products, using X-ray crystallography and ab initio calculations. (C) 2016 Elsevier Ltd. All rights reserved.
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