154902-54-2

Upstream product

• 56613-80-0 D-2-phenylglycinol 
• 123-11-5 4-methoxy-benzaldehyde 
• 52010-97-6 4-(hydroxylmethyl)benzaldehyde 

Downstream Products

• 154777-13-6 (4R-1'R)-4-(2'-hydroxy-1'-phenylethylamino)-4-(4-methoxyphenyl)butanal dimethyl acetal 
• 3717-21-3 p-methoxyl benzaldoxime 
• 182316-01-4 (5R)-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one-N-oxide 
• 182316-07-0 (1R,2S,6S,9R)-8-aza-7,11-dioxa-9-phenyltricyclo[6.4.0.0^2,6]dodecan-12-one 
• 321174-47-4 (R)-α-(hydroxymethyl)benzylhydroxylamine 
• 154777-24-9 (2R,5R,1'R)-N-2'-hydroxy-1'-phenylethyl-2,5-bis(4-methoxyphenyl)pyrrolidine 
• 154777-16-9 (2R,5S,8R)-8-(4-methoxyphenyl)-2-phenyl-1-aza-4-oxabicyclo<3.3.0>octane 

Relevant academic research and scientific papers

Indium-mediated asymmetric barbier-type allylation of aldimines in alcoholic solvents: Synthesis of optically active homoallylic amines

(Chemical Equation Presented) Chiral aldimines derived from phenylglycinol were diastereoselectively allylated with indium powder/allyl bromide in alcoholic solvents. Both aliphatic and aromatic aldimines provided good yield of the desired products with h

Design, synthesis, and 1,3-dipolar cycloaddition of (5R)- [and (5S)]-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxides as chiral (E)-geometry-fixed α-alkoxycarbonylnitrones

Optically pure (5R)- [and (5S)]-5,6-dihydro-5-phenyl-2H-1,4-oxazin-2-one N-oxides [(5R)- and (5S)-2] were designed as chiral (E)-geometry-fixed α-alkoxycarbonylnitrones 1. The nitrones (5R)- and (5S)-2 were synthesized by three-step oxidation of (R)- and (S)-phenylglycinols [(R)- and (S)-3], condensation of the resulting (R)- and (S)-2-hydroxylamino-2-phenylethanols [(R)- and (S)-5] with glyoxylic acid, and cyclization of the intermediary nitrones (R)- and (S)-6b. The nitrone (5R)-2 reacted with olefins 7-14 under mild conditions to afford the corresponding cycloadducts 15-22 as the main products via the least sterically demanding exo modes. Cycloadduct 30 obtained from (5S)-2 and cyclopentadiene was effectively elaborated to (1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-en-3-one (28), the key synthetic intermediate of carbocyclic polyoxin C.

Diastereoselective addition of chiral imines and 1,3-oxazolidines with Grignard reagents; asymmetric synthesis of (R)-2-aryl- and (R,R)-2,5-bis(aryl)pyrrolidines

Asymmetric syntheses of (R)-2-aryl- and (R,R)-2,5-bis(aryl)pyrrolidines were described starting from chiral aromatic imines derived from (R)-phenylglycinol, in which the diastereoselective additions of Grignard reagents to the chiral imines and 1,3-oxazol

DIASTEREOSELECTIVE ADDITION OF ORGANOMETALLIC REAGENTS TO CHIRAL IMINES AND 1,3-OXAZOLIDINES

The reaction of MeLi or MeMgBr with chiral aromatic imines and 2-aryl-1,3-oxazolidines derived from (R)-phenylglycinol afforded with good diastereoselectivity (R,R)-amines from imines, but the (R,S)-amines from 1,3-oxazolidines, respectively.

Diastereoselective Strecker Synthesis using α-Phenylglycinol as Chiral Auxiliary

Use of α-phenylglycinol as chiral auxiliary in Strecker synthesis ensures high diastereoselectivity and its easy removal by oxidative cleavage allows large scale preparation of optically active α-amino acids.