Diastereoselective [Cu(MeCN)4BF4/BF3·Et2O]-Catalyzed Cyclopropenation of Alkynes: Asymmetric Synthesis of β-Amino-α-cyclopropenyl Phosphonates

Autor: Haihong Ge, Shuang Liu, Yan Cai, Zenghui Gao, Siyi Du, Zhiwei Miao, Guixian Xie
Jazyk: angličtina
Rok vydání: 2017
Předmět:
Zdroj: SynOpen, Vol 01, Iss 01, Pp 0068-0075 (2017)
Druh dokumentu: article
ISSN: 2509-9396
DOI: 10.1055/s-0036-1590969
Popis: Abstract The diastereospecific formation of β-amino-α-cyclopropenyl phosphonates has been achieved in moderate yields from the cyclopropenation of 1-alkynes with dialkyl α-diazophosphonates. The reaction was performed by using a combined catalyst consisting of Cu(MeCN)4BF4 and BF3·Et2O as additive in dichloromethane at 40 °C. A possible mechanism for the reaction has been proposed to explain the origin of the activation and the asymmetric induction. This method provides a versatile approach to β-amino-α-cyclopropenylphosphonates containing a quaternary stereogenic center with good efficiency and diastereoselectivity.
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