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Radical zinc-atom-transfer-based carbozincation of haloalkynes with dialkylzincs
- Source :
- Beilstein Journal of Organic Chemistry, Vol 9, Iss 1, Pp 236-245 (2013)
- Publication Year :
- 2013
- Publisher :
- Beilstein-Institut, 2013.
-
Abstract
- The formation of alkylidenezinc carbenoids by 1,4-addition/carbozincation of dialkylzincs or alkyl iodides based on zinc atom radical transfer, in the presence of dimethylzinc with β-(propargyloxy)enoates having pendant iodo- and bromoalkynes, is disclosed. Formation of the carbenoid intermediate is fully stereoselective at −30 °C and arises from a formal anti-selective carbozincation reaction. Upon warming, the zinc carbenoid is stereochemically labile and isomerizes to its more stable form.
Details
- Language :
- English
- ISSN :
- 18605397
- Volume :
- 9
- Issue :
- 1
- Database :
- Directory of Open Access Journals
- Journal :
- Beilstein Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsdoj.0443e74070b64ea1bc0ae5c6dc71abe0
- Document Type :
- article
- Full Text :
- https://doi.org/10.3762/bjoc.9.28