First and unexpected synthesis of macrocyclic cyclophane-based unusual alpha-amino acid derivatives by phosphazene base without high dilution conditions

Bioorganic & Medicinal Chemistry Letters
Sambasivarao KothaVasantha Pattabhi

Abstract

First synthesis of a macrocylic cyclophane-based unusual alpha-amino acid derivative 11 by coupling of ethyl isocyanoacetate with 1,2-bis(4-bromomethylphenyl)ethane under phase-transfer catalysis (PTC) conditions. Phosphazene base such as 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) is useful to improve the yield of cyclophane derivative without high dilution conditions.

References

Apr 13, 1999·Bioorganic & Medicinal Chemistry·R Kaul, P Balaram
May 18, 2000·The Journal of Organic Chemistry·S Kotha, E Brahmachary
Feb 15, 2001·Accounts of Chemical Research·T M Trnka, R H Grubbs
Apr 17, 2001·Chemistry : a European Journal·A H Hoveyda, R R Schrock

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Citations

Oct 2, 2015·Beilstein Journal of Organic Chemistry·Sambasivarao KothaGopalkrushna T Waghule
Jul 9, 2010·Chemical Reviews·Anton V GulevichValentine G Nenajdenko
Jun 27, 2012·The Journal of Organic Chemistry·Sambasivarao Kotha, Gopalkrushna T Waghule

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