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- Title
Enantioselective Allylation of β-Haloacrylaldehydes: Formal Total Syntheses of Pteroenone and Antillatoxin.
- Authors
Koukal, Petr; Ulč, Jan; Nečas, David; Kotora, Martin
- Abstract
A comparative study of the catalytic allylations and crotylations of ( E)- and ( Z)-haloacrylaldehydes by Lewis bases (chiral N, N′-dioxides) and Brønsted acids (chiral phosphoric acids) was undertaken. The reactions proceeded with high enantio- and diastereoselectivities with slightly better asymmetric induction observed in the case of N, N′-dioxide catalysis. The formed enantioenriched chiral unsaturated haloalcohols could be considered general building blocks, as they could be used in the syntheses of more complex natural products possessing substituted 1,3-diene fragments. This was exemplified by the formal total syntheses of pteronenone and antillatoxin.
- Subjects
ALLYLATION; CHEMICAL synthesis; LEWIS bases; PHOSPHORIC acid; HALOHYDRINS
- Publication
European Journal of Organic Chemistry, 2016, Vol 2016, Issue 12, p2110
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201600286