Regiodivergent Halogenation of (E)-beta-Chlorovinyl Ketones via Soft alpha-Vinyl Enolization Strategy
- Authors
- Kim, Hun Young; Lee, Seokwoo; Kim, Sanghee; Oh, Kyungsoo
- Issue Date
- Feb-2015
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.17, no.3, pp 450 - 453
- Pages
- 4
- Journal Title
- ORGANIC LETTERS
- Volume
- 17
- Number
- 3
- Start Page
- 450
- End Page
- 453
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/9873
- DOI
- 10.1021/ol5034354
- ISSN
- 1523-7060
1523-7052
- Abstract
- The soft a-vinyl enolization of (E)-beta-chlorovinyl ketones was investigated in the presence of various halogen electrophiles. Depending on the nature of halogen electrophiles, the selective formation of three products, namely alpha,alpha-dichloropropargyl ketones, alpha,gamma-dihaloallenyl ketones, and 3-halofurans, was observed. The observed regiodivergent nucleophilic pathways of (E)-beta-chlorovinyl ketones demonstrate the diversity-oriented synthesis strategy in which the nucleophilic reactivity of (E)-beta-chlorovinyl ketones can be selectively modulated by the choice of suitable hard and soft electrophiles.
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Collections - College of Pharmacy > School of Pharmacy > 1. Journal Articles
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