Diphenylprolinol triethylsilyl ether

Scheme 2.11 Three-component reaction of aldehydes, protected a-cyanoglycine esters and a,p-unsaturated aldehydes catalysed by a combination of chiral diphenylprolinol triethylsilyl ether and an oxime.

Organocatalytic, enantioselective cascade Michael-aldol condensation catalyzed by readily available (5 )-diphenylprolinol triethylsilyl ether gives synthetically useful, highly functionalized chiral cyclopentenes (Scheme 6.12) [14],... 

These problems could be minimized by the use of bulky and readily enolizable malonates and a sterically hindered organocatalyst such as 145. Accordingly, substrate 144, bearing a nucleophilic malonate and an electrophilic aldehyde group, was utilized for the cascade Michael-aldol condensation process (Scheme 1.54) [90]. The process is catalyzed efficiently by readily available (S)-diphenylprolinol triethylsilyl ether 145 to give synthetically useful, highly functionalized chiral cyclopentenes. 

The triethylsilyl ether of a,a-diphenylprolinol 2B induces the Michael-aldol reaction tandem that combines A -protected o-aminobenzaldehydes and 2-alkenals to form chiral 2-substituted 3 -formyl-1,2-dihydroquinolines. ... 

Scheme 2.12 Pseudo three-component domino Michael-aldol reaction catalysed by a combination of chiral diphenylprolinol trimethyl- or triethylsilyl ether and a thiourea.

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