Ylides are neutral polar molecule possessing positively charged heteroatoms (P, Se, O, S, and
N) and carbon having unshared pair of electrons. They are one of the important reactive
intermediates in organic synthesis, which are known to undergo several synthetically useful
transformations.1 Generation of ylides from α-diazo ester, Lewis base and transition metal is
most effective method for the synthesis of structurally complex molecules.2 In this regards, insitu
trapping of ylide with various electrophiles such as carbonyl compounds and its derivatives
for the construction of complex frameworks having quaternary center3, which is ubiquitous
structural elements found in numerous biologically active natural products, has gained
significant attention in recent decades. Having said, this presentation will deal with various
methods of generation and trapping of ylides with polar double bonds followed by proposed
methods for trapping of ylides with various electrophiles.
Reference:
[1] a) David M. Hodgson, Francoise Y. T. M. Pierard, Paul A. StuppleChem. Soc. Rev. 2001, 30, 50; b)Padwa,
A. Chem Soc. Rev. 2009, 38, 3072.
[2] Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods For Organic Synthesis with Diazo
Compounds: From Cyclopropanes To Ylides; Wiley: New York, 1998.
[3] a) Guo, X.; Hu, W. Acc. Chem. Res.2013, 46, 2427; b) Xiao, Q.; Zhang, Y.; Wang, J. Acc. Chem. Res.2013,
46, 236.