16354-97-5

Upstream product

• 102563-44-0 (R)-2,2-Dimethyl-4-dimethylaminocarbonyl-1,3-dioxolane 
• 100-58-3 phenylmagnesium bromide 
• 170164-81-5 (2R)-2,3-O-isopropylidene-N-methoxy-N-methylpropanamide 
• 201420-74-8 [(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol 
• 73945-73-0 (R)-2,3-o-isopropylidene-D-glyceroyl chloride 
• 114746-70-2 (R)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 52373-72-5 methyl (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 

Downstream Products

• 16354-98-6 (R)-2,3-dihydroxy-1-phenylpropan-1-one 
• 877869-69-7 (Z)-(4S)-methyl 4,5-dihydroxy-4,5-O-isopropylidene-2-methyl-3-phenyl-2-pentenoate 
• 1034170-12-1 (5S)-1-(tert-butoxycarbonyl)-5-{(R)-trimethylsilanyloxy[(R)-(2,2-dimethyl-1,3-dioxolan-4-yl)](phenyl)methyl}-1H-pyrrol-2(5H)-one 
• 201420-74-8 [(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol 
• 16354-89-5 (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol 
• 16354-91-9 (S)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol 

Relevant academic research and scientific papers

Further uses of pyrrole-based dienoxysilane synthons: A full aldol approach to azabicyclo[x.2.1]alkane systems

Two racemic 2-azabicyclo[2.2.1]heptane structures, 15 and 21, and two chiral non-racemic 6-azabicyclo[3.2.1]octane representatives, 28 and 36, have been synthesized starting from 1-(tert-butoxycarbonyl)-2-(tert- butyldimethylsilyloxy)-pyrrole (TBSOP, 5) and suitable ketones, 9, 16, 22 and 29. 2-Azabicycle 15 was then elaborated to racemic cyclopentane amino acid 38, while 6-azabicycle 36 served to access the enantiomerically pure normorphan-type structure 40. For all substrates, a uniform synthetic scheme was implemented based on the combination of two diastereoselective aldol-type carbon-carbon bond-forming reactions, the efficiencies of which were secured by appropriate aldol-stabilizing steps. A mechanistic rationale accounting for the markedly diastereoselective character of the key Mukaiyama aldol reactions between TBSOP and the ketone acceptors has been postulated that involves hetero-Diels-Alder transition-state structures in which the preference for endo versus exo addition is governed by the electronic nature of the substituents in the ketone substrates. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

A route to homochiral (S)-O-methyl mandelic acid and related α-alkoxy carboxylic acids from isopropylidene glycerol

An improved synthesis of the useful ketones 7 is described. These ketones are then further modified via a highly stereospecific reduction to give homochiral α-alkoxy carboxylic acids which are useful chiral auxiliaries and intermediates.