Abstract
A one-pot direct reductive allylation protocol has been developed for the synthesis of secondary amines by using titanium hydride and an allylzinc reagent. This protocol is applicable to a broad range of substrates, including acyclic amides, benzamides, α,β-unsaturated amides, and lactams. The stereochemical outcome obtained from the reaction with crotylzinc reagent suggested that the allylation reaction proceeds through a six-membered cyclic transition state. A total synthesis of (-)-castoramine was accomplished by following this protocol for the highly stereoselective construction of contiguous stereocenters.
Original language | English |
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Pages (from-to) | 1786-1790 |
Number of pages | 5 |
Journal | Synlett |
Volume | 29 |
Issue number | 13 |
DOIs | |
Publication status | Published - 2018 Jun 26 |
Keywords
- alkaloids
- allylation
- amides
- amines
- reduction
- total synthesis
ASJC Scopus subject areas
- Organic Chemistry