108794-01-0

Upstream product

• 187737-37-7 propene 
• 84312-20-9 (1R,3R,4S)-8-phenylmenthyl glyoxylate 
• 106-95-6 allyl bromide 
• 24850-33-7 allyltributylstanane 
• 108794-12-3 <1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl dihydroxyacetate 
• 80595-59-1 bromoacetic acid (-)-8-phenylmenthol ester 
• 104197-95-7 (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl nitrooxyacetate 
• 72526-00-2 (-)-8-phenylmenthyl acrylate 
• 65253-04-5 (-)-8-phenylmenthol 
• 89-82-7 pulegone 
• 56680-79-6 allyloxyacetyl chloride 
• 109385-12-8 Allyloxy-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 

Relevant academic research and scientific papers

Enantioselective synthesis of unsaturated α-hydroxy acids

(S)- and (R)-2-Hydroxyhex-5-enoic acid and (S)- and (R)-2-hydroxyhept- 6-enoic acid were prepared in excellent yields and enantiomeric excesses (>99% ee) from the corresponding α-keto esters by the enzyme catalysed hydrolysis of the ester and reduction of the ketone in a single pot process. The enantioselective synthesis of (S)-2-hydroxypent-4-enoic acid was achieved via reaction of the reagent derived from allyl bromide and indium metal with the hydrate of 8-phenylmenthyl glyoxalate in water.

Trifluoromethane sulphonic acid: A Bronsted acid catalyst for the addition of allyltributylstannanes to carbonyl compounds in water

Trifluoromethane sulphonic acid catalyses the addition of allyltributylstannane to carbonyl compounds in water to give the corresponding homoallylic alcohols in high yields.

Diastereoselective allylation of N-glyoxyloyl-(2R)-bornane-10,2-sultam and (1R)-8-phenylmenthyl glyoxylate: Synthesis of (2S,4S)-2-hydroxy-4-hydroxymethyl- 4-butanolide

The diastereoselective addition of allylsilanes and allylstannanes to N-glyoxyloyl-(2R)-bornane-10,2-sultam 1 and (1R)-8-phenylmenthyl glyoxylate 7 in the presence of Lewis acids has been studied. We obtained diastereoselectivities up to 84% and 94% for the allylation of 2 and 7, respectively. The application of the allylation products of 1 or 2 in the synthesis of 4-butanolides, for example (2S,4S)-2-hydroxy-4-hydroxymethyl-4- butanolide 13 is presented.

Asymmetric -Wittig Rearrangement Involving a Chiral Ester Enolate Terminus. A Chiral Synthesis of erythro-α-Hydroxy-β-alkyl Carboxylic Acid Derivatives

The title rearrangement of the (E-2-alkenyloxy)acetic esters derived from (-)-8-phenylmenthol has been shown to afford the corresponding 3-alkyl-2-hydroxy-4-pentenoic ester with an extremly high level of diastereoface selection (95-97percent de) along with a high erythro selectivity (90-93percent).

ASYMMETRIC INDUCTION IN THE ENE REACTION OF GLYOXYLATE ESTERS OF 8-PHENYLMENTHOL

We recently communicated (J.K.Whitesell, A.Bhattacharya, D.A.Aguilar and K.Henke, J.Chem.Soc.Chem.Commun. 989 (1982)) a highly efficient and effective method for the control of absolute stereochemistry through asymmetric induction in the ene reaction the chiral glyoxylate 1 with alkenes.We now have accumulated sufficient information on this process in terms of both its mechanistic details as well as its scope and applicability to a variety of situations that warrants a more complete presentation of these reactions.