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Stereoselective allylation reactions of acyclic and chiral α-amino-β-hydroxy aldehydes 3: Total synthesis of (+)-1-epi-castanospermine

Author:
Myeong, In-Soo, Ham, Won-Hun
Source:
Tetrahedron 2019 v.75 no.28 pp. 3832-3839
ISSN:
0040-4020
Subject:
aldehydes, allylation, chemical structure, stereoselectivity
Abstract:
Stereoselective allylation reactions of acyclic, chiral α-amino-β-hydroxy aldehydes containing four contiguous stereocenters were conducted. Allylation mediated by MgBr2∙OEt2 afforded the anti-product. A plausible mechanism of the allylation reaction is also described. The resulting allylation product was used for the total synthesis of (+)-1-epi-castanospermine.
Agid:
6465753