66867-29-6

Upstream product

• 151-50-8 potassium cyanide 
• 100-52-7 benzaldehyde 
• 79-22-1 methyl chloroformate 
• 773837-37-9 sodium cyanide 
• 17640-15-2 methyl cyanoformate 
• 28549-12-4 (S)-mandelonitrile 

Downstream Products

• 4063-69-8 (R)-2-(methoxycarbonyloxy)-2-phenylacetic acid 
• 17199-29-0 (S)-Mandelic acid 
• 611-71-2 (R)-Mandelic Acid 
• 86013-50-5 (R)-(2-hydroxy-2-phenyl-ethyl)carbamic acid tert-butyl ester 
• 281670-47-1 (S)-(2-hydroxy-2-phenyl-ethyl)carbamic acid tert-butyl ester 
• 64-04-0 phenethylamine 

Relevant academic research and scientific papers

Catalyst-free DMSO-promoted synthesis of cyanohydrin carbonates from aldehydes

A variety of cyanohydrin carbonates were readily prepared from aldehydes with cyanoformate in DMSO using no catalyst in a convenient one-pot procedure.

Enantioselective cyanoformylation of aldehydes mediated by BINOLAM-AlCl as a monometallic bifunctional catalyst

BINOLAM-AlCl's, binaphthoxide aluminium chloride species generated in situ from either (R)- or (S)-3,3′-bis(diethylaminomethyl)-2,2′-dihydroxy-1,1′- binaphthalene (BINOLAM) behave as Lewis acid-Lewis base (LA-LB) catalysts in the enantioselective addition of methyl cyanoformate to aldehydes at room temperature, thereby leading to the asymmetric synthesis of (S)- or (R)-O-methoxycarbonyl cyanohydrins, respectively.

Consecutive reactions to construct tricarbonyl compounds and synthetic applications thereof

Lithium anions derived from O-carbonate-protected cyanohydrins undergo conjugate addition to cycloalkenones with the concomitant transfer of the alkoxycarbonyl group to produce tricarbonyl compounds. These products offer numerous possibilities for further

TBD- or PS-TBD-catalyzed one-pot synthesis of cyanohydrin carbonates and cyanohydrin acetates from carbonyl compounds

Cyanation reactions of carbonyl compounds with methyl cyanoformate or acetyl cyanide catalyzed by 5 mol % of 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) were examined. Using methyl cyanoformate, the corresponding cyanohydrin carbonates were readily obtained in high yield for aromatic and aliphatic aldehydes and ketones. Similar results were obtained when acetyl cyanide was used as the cyanide source. The polymer-supported catalyst, PS-TBD, also acted as a good catalyst for this reaction. PS-TBD was easily recovered and reused with minimal activity loss.

Tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP): Efficient catalysts for the cyanosilylation and cyanocarbonation of aldehydes and ketones

A variety of aldehydes and ketones were transformed to their corresponding cyanohydrin silyl ethers in good to excellent yields in the presence of 1-5 mol% of tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP). Cyanohydrin carbonates were also readily prepared using 5-10 mol% of TTMPP as an organocatalyst.

Enantioselective cyanoformylation of aldehydes organocatalyzed by recyclable cinchonidine ammonium salts

Enantiomerically enriched O-methoxycarbonyl cyanohydrins were obtained using an enantioselective addition of methyl cyanoformate to aldehydes organocatalyzed by a dimeric anthracenyldimethyl-derived cinchonidine ammonium salt (1 mol % catalyst loading) in the presence of substoichiometric amounts of triethylamine (20 mol %). Aromatic and heteroaromatic aldehydes usually afford high enantioselectivities (up to 96%) and quantitative yields of the corresponding O-methoxycarbonyl cyanohydrins, whereas aliphatic and α,β-unsaturated aldehydes give lower enantioselectivities (up to 60%) in high yields. The observed sense of the enantioselection was always the same, and the organocatalyst was almost quantitatively recovered by ether-promoted precipitation without any loss of activity. The use of resin-supported cinchonidine-derived ammonium salts as an organocatalyst in this transformation was also explored.

Enantioselective cyanoformylation of aldehydes using a recyclable dimeric cinchonidine ammonium salt as an organocatalyst

A dimeric anthracenyldimethyl-derived cinchonidine ammonium salt is used as a chiral organocatalyst in the enantioselective addition of alkyl cyanoformates to aldehydes in the presence of substoichiometric amounts of triethylamine. Quantitative yields and

Enantioselective and diastereoselective syntheses of cyanohydrin carbonates

A new and general synthesis of alkyl cyanoformates is presented starting from the appropriate alcohol and oxalyl chloride. This is used to prepare enantiomerically pure cyanoformates from enantiomerically pure primary and secondary alcohols. Optimal condi

Enantioselective synthesis of O-methoxycarbonyl cyanohydrins: Chiral building blocks generated by bifunctional catalysis with BINOLAM-AlCl

(R)- or (S)-BINOLAM-AlCl, generated in situ, work as bifunctional catalysts in promoting the enantioselective cyanoalkoxycarbonylation of aldehydes. The reaction is wide in scope and the mechanistic evidence gathered suggests the intervention of an indirect process involving enantioselective hydrocyanation by HCN, followed by O-alkoxycarbonylation. The resultant O-alkoxycarbonyl cyanohydrins are shown to be important chiral building blocks for synthesis. Chemoselective hydrolysis can thus be directed either to provide enantioenriched β-hydroxy esters, or acids, or instead to give O-methoxycarbonyl β-hydroxy acids, esters, or amides. In addition, the enantiopure cyanocarbonates can be converted into β-amino alcohols by reduction with lithiumaluminium hydride. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Cyanide ion cocatalysis in Ti(salen) catalysed asymmetric cyanohydrin carbonate synthesis

In the presence of potassium cyanide or the potassium cyanide/18-crown-6 complex as a cocatalyst, 1-2 mol% of titanium(salen) complex 1 catalyses the asymmetric addition of achiral cyanoformates to aldehydes, giving cyanohydrin carbonates with high enanti