Highly enantioselective zinc/amino alcohol-catalyzed alkynylation of aldehydes.
Meeting the challenge: The zinc/amino alcohol catalyzed enantioselective addition of terminal alkynes to aldehydes is effective with both phenylacetylene and methyl propiolate, leading to chiral secondary propargyl alcohols with very high enantioselectivity (see scheme).
Zhong
Jiang-Chun
JC
Department of Applied Chemistry, China Agricultural University, Beijing, China.
Hou
Shi-Cong
SC
Bian
Qing-Hua
QH
Yin
Min-Min
MM
Na
Ri-Song
RS
Zheng
Bing
B
Li
Zhi-Yuan
ZY
Liu
Shang-Zhong
SZ
Wang
Min
M
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003521:Cyclopropanes / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D000447:Aldehydes; D000480:Alkynes; D000605:Amino Alcohols; D003521:Cyclopropanes; D020005:Propanols; C028255:propargyl alcohol; D015032:Zinc