Efficient synthesis of β’-amino-α,β-unsaturated ketones

• Isabelle Abrunhosa-Thomas,
• Aurélie Plas,
• Nishanth Kandepedu,
• Pierre Chalard and
• Yves Troin

Beilstein J. Org. Chem. 2013, 9, 486–495, doi:10.3762/bjoc.9.52

• –Emmons reaction as a key step for generating the β'-amino-α,β-enones, permits access to a range of substrates under mild conditions and in moderate to high yield. Keywords: β’-amino-α,β-unsaturated ketones; Horner–Wadsworth–Emmons reaction; stereoselective synthesis; Introduction Compounds

• did not allow the use of a wide range of functional groups and sometimes gave bad overall yields, we devised a general and simple method to easily access a variety of β’-amino-α,β-unsaturated ketones by a more convenient route using the Horner–Wadsworth–Emmons reaction [19][20] as the key step, as

• , R2CO2Cl, CH2Cl2/H2O; (d) BuLi, (EtO)2P(O)Me, THF, −78 °C. Optimization of conditions for the Horner–Wadsworth–Emmons reaction. Formation of the ketophosphonates 13. Horner–Wadsworth–Emmons optimal conditions for 15a. Formation of the β’-amino-α,β-unsaturated ketones 15 under Ba(OH)2 conditions