Tetrahedron p. 8665 - 8678 (1993)
Update date:2022-08-04
Topics:
Ezquerra, Jesus
Pedregal, Concepcion
Rubio, Almudena
Yruretagoyena, Belen
Escribano, Ana
Sanchez-Ferrando, Francisco
The lithium enolates of N-Boc protected pyroglutamic ethyl or tert-butyl esters react with electrophiles in good yield without epimerization of the chiral centre.With benzyl bromides the process is stereospecific, yielding exclusively the trans isomer.However, with other reactive electrophiles a 2:1 tans/cis diastereometric mixture was obtained, regardless of the steric bulk of the ester group.
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Doi:10.1002/jhet.5570380232
(2001)Doi:10.1016/S0957-4166(00)80435-8
(1993)Doi:10.1021/ja411535q
(2014)Doi:10.1016/S0040-4039(00)61615-5
(1993)Doi:10.1021/jo00067a067
(1993)Doi:10.1016/0022-328X(93)83155-O
(1993)
