118965-95-0Relevant academic research and scientific papers
Practical and robust method for regio- and stereoselective preparation of (E)-ketene tert-butyl TMS acetals and β-ketoester-derived tert-butyl (1Z,3E)-1,3-bis(TMS)dienol ethers
Okabayashi, Tomohito,Iida, Akira,Takai, Kenta,Nawate, Yuuya,Misaki, Tomonori,Tanabe, Yoo
, p. 8142 - 8145 (2008/02/12)
(Chemical Equation Presented) We developed an efficient, practical, robust method for the regio- and stereoselective preparation of (E)-ketene trimethylsilyl acetals (KSAs) derived from tert-butyl esters 1. The reaction was performed under convenient reac
DIBENZYLAMINOACETATES AS USEFUL SYNTHETIC EQUIVALENTS OF GLYCINE IN THEi SYNTHESIS OF α-AMINO-β-HYDROXYACIDS
Guanti, Giuseppe,Banfi, Luca,Narisano, Enrica,Scolastico, Carlo
, p. 3671 - 3684 (2007/10/02)
The stereochemical course of three new simple methodologies for the preparation of α-amino-β-hydroxyacids starting from dibenzylaminoacetates as synthetic equivalents of glycine is described.While the aldol-type condensation via lithium enolates gave results highly dependent on the aldehyde employed, producing in some cases diastereoselectivities up to 5:1 for the anti isomers, the acid-catalysed aldol condensation of silyl ketene acetals yielded predominantly syn adducts with selectivities from 5:1 to 32:1.Finally the acylation-reduction procedure gave the best results in terms of yields and stereoselectivities, affording syn isomers with excellent induction ( 13:1).
