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Copper‐Catalyzed Amine–Alkyne–Alkyne Addition Reaction: An Efficient Method For the Synthesis of γ,δ‐Alkynyl‐β‐amino Acid Derivatives
Author(s) -
Zhou Lei,
Shuai Qi,
Jiang Huanfeng,
Li ChaoJun
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901416
Subject(s) - alkyne , amine gas treating , chemistry , diastereomer , catalysis , combinatorial chemistry , copper , organic chemistry , medicinal chemistry
A simple and efficient method for the synthesis of γ,δ‐alkynyl‐β‐amino acid derivatives by a copper‐catalyzed three‐component amine–alkyne–alkyne addition reaction was developed. Various γ,δ‐alkynyl‐β‐amino acid derivatives were synthesized in moderate to good yields in one step. With chiral prolinol derivatives employed as the amine component, excellent diastereoselectivities (up to >99:1 diastereomeric ratio (dr)) were obtained. The scope of the reaction and further transformations of the resulting amino acid derivatives, such as deprotection and cyclization are also described.