Kowalski ester homologation

The Kowalski Ester Homologation provides a similar conversion (C. Kowalski, M. S. Haque, Journal of Organic Chemistry 1985, 50, 5140)... 

Other references related to the Kowalski ester homologation was cited in the literature. ... 

Rajarathnam E. Reddy and Conrad J. Kowalski 146 ETHYL 1 -NAPHTHYLACETATE ESTER HOMOLOGATION VIA YNOLATE ANIONS... 

Ester Homologation via Ynolate Anions Methyl 3-Cyc1ohexeny1acetate C. J. Kowalski and S. Sakdarat, Synthetic Chemistry Department,... 

For a homologation of carboxylic esters RCOOEt —> RCH2COOEt, which goes by an entirely different pathway, see Kowalski, CJ. Haque, M.S. Fields, K.W. J. Am. Chem. 

Often, esters are homologated by one carbon using the diazomethane-based Amdt-Eistert procedure. Kowalski homologation, addition of the inexpensive dibromomethane followed by -elimination, is a more scalable alternative. Timothy Gallagher of the University of Bristol recently reported (J. Org. Chem. 2004, 69, 4849) the use of Kowalski homologation to prepare P-amino esters from a-amino esters, including the conversion of 3 to 4. Note that the transformation can be carried out without protection of the OH, and that it proceeds without loss of stereochemical integrity. 

During the total synthesis of (-)-cylindrocyclophane F, A.B. Smith et al. used the Danheiser benzannuiation to construct the advanced aromatic intermediate for an olefin metathesis dimerization reaction. The starting material triisopropylsilyloxyalkyne was synthesized from the corresponding ethyl ester using the Kowalski two-step chain homologation. ... 

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