Abstract
The CrCl2-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-α-chloro- and (Z)-α-bromo-α,β-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis.
Original language | English (US) |
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Pages (from-to) | 4359-4361 |
Number of pages | 3 |
Journal | Tetrahedron Letters |
Volume | 49 |
Issue number | 28 |
DOIs | |
State | Published - Jul 7 2008 |
Keywords
- Aldehydes
- Chromium
- Enals
- Homologation
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry