Formation of diethyl 2-amino-1-cyclopentenylphosphonates: A simple synthesis with a unique mechanism

Abed Al Aziz Al Quntar; Hemant Kumar Srivastava; Morris Srebnik; Artem Melman; Rachel Ta-Shma; Avital Shurki

doi:10.1021/jo070535b

Formation of diethyl 2-amino-1-cyclopentenylphosphonates: A simple synthesis with a unique mechanism

Abed Al Aziz Al Quntar
, Hemant Kumar Srivastava
, Morris Srebnik^*
, Artem Melman
, Rachel Ta-Shma
, Avital Shurki

^*Corresponding author for this work

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

(Chemical Equation Presented) Reaction of diethyl 5-chloro-1- pentynylphosphonate with primary and secondary amines produces novel 2-amino-1-cyclopentenylphosphonat.es, 1, in excellent isolated yields (79-88%). Calculations supported by experimental facts point to a two-step mechanism: an initial amine addition to give a zwitterionic intermediate followed by cyclization and proton transfer. Calculations rule out the formation of an enamine as an intermediate.

Original language	English
Pages (from-to)	4932-4935
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	72
Issue number	13
DOIs	https://doi.org/10.1021/jo070535b
State	Published - 22 Jun 2007

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abstract = "(Chemical Equation Presented) Reaction of diethyl 5-chloro-1- pentynylphosphonate with primary and secondary amines produces novel 2-amino-1-cyclopentenylphosphonat.es, 1, in excellent isolated yields (79-88\%). Calculations supported by experimental facts point to a two-step mechanism: an initial amine addition to give a zwitterionic intermediate followed by cyclization and proton transfer. Calculations rule out the formation of an enamine as an intermediate.",

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T1 - Formation of diethyl 2-amino-1-cyclopentenylphosphonates

T2 - A simple synthesis with a unique mechanism

AU - Al Quntar, Abed Al Aziz

AU - Srivastava, Hemant Kumar

AU - Srebnik, Morris

AU - Melman, Artem

AU - Ta-Shma, Rachel

AU - Shurki, Avital

PY - 2007/6/22

Y1 - 2007/6/22

N2 - (Chemical Equation Presented) Reaction of diethyl 5-chloro-1- pentynylphosphonate with primary and secondary amines produces novel 2-amino-1-cyclopentenylphosphonat.es, 1, in excellent isolated yields (79-88%). Calculations supported by experimental facts point to a two-step mechanism: an initial amine addition to give a zwitterionic intermediate followed by cyclization and proton transfer. Calculations rule out the formation of an enamine as an intermediate.

AB - (Chemical Equation Presented) Reaction of diethyl 5-chloro-1- pentynylphosphonate with primary and secondary amines produces novel 2-amino-1-cyclopentenylphosphonat.es, 1, in excellent isolated yields (79-88%). Calculations supported by experimental facts point to a two-step mechanism: an initial amine addition to give a zwitterionic intermediate followed by cyclization and proton transfer. Calculations rule out the formation of an enamine as an intermediate.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

Formation of diethyl 2-amino-1-cyclopentenylphosphonates: A simple synthesis with a unique mechanism

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