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Isothiocyanate Strategy for the Synthesis of Quaternary α‐Amino Acids Bearing a Spirocyclic Ring System
Author(s) -
Frankowski Sebastian,
Gajda Tadeusz,
Albrecht Łukasz
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701642
Subject(s) - chemistry , moiety , isothiocyanate , ring (chemistry) , nucleophile , yield (engineering) , amino acid , nucleophilic addition , michael reaction , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry , materials science , metallurgy
This study demonstrates that isothiocyanates derived from α‐substituted α‐amino acids are useful building blocks in the heteroannulation reactions with electron‐deficient olefins. The developed strategy proceeds in a cascade manner and involves Michael addition followed by a cyclization via nucleophilic addition. Target, spirocyclic heterocycles bearing either a quaternary α‐amino acid moiety or α‐aminophosphonate group have been efficiently synthesized in very high yield (up to 99%) and with excellent stereocontrol. The usefulness of heterocycles obtained has been demonstrated in selected transformations.