198642-79-4

Upstream product

• 6683-92-7 1-phenylpentan-2-one 
• 55666-17-6 (1E)-1,4-pentadienylbenzene 
• 794525-95-4 (S)-1-[2-(p-tolylsulfinyl)phenyl]pentan-2-one 

Downstream Products

• 736144-02-8 ((S)-1-Hydroxymethyl-pentyl)-carbamic acid (S)-1-benzyl-butyl ester 

Relevant academic research and scientific papers

A general method for the synthesis of nonracemic trans-epoxides: Concise syntheses of trans-epoxide-containing insect sex pheromones

A general method for the synthesis of chiral nonracemic frans-epoxides has been developed that provides rapid access to alkyl-, alkenyl-, alkynyl-, and phenyl-substituted frans-epoxides from aldehydes. This methodology has also been applied in concise and

Screening on the use of Kluyveromyces marxianus CBS 6556 growing cells as enantioselective biocatalysts for ketone reductions

The versatility of Kluyveromyces marxianus CBS 6556 growing cells in the enantioselective reduction of ketone functionalities to the corresponding alcohols was exploited. In particular, methyl ketones were reduced to (S)-alcohols with ees of up to 96%. Longer chain alkyl ketones afforded, under the same experimental condition, (R)-alcohols with an ee of up to 84%. Interestingly, carbon-carbon double and the triple bonds can also be reduced in the presence of Kluyveromyces marxianus CBS 6556 yeast. A cyclic ketone, such as 2-tetralone, was also quantitatively reduced to its corresponding (S)-alcohol with ee = 76%.

Remote stereocontrol by sulfinyl groups: Reduction of δ- ketosulfoxides

(Chemical Equation Presented) The reduction of δ-ketosulfoxides constitutes the first evidence of the efficiency of the sulfinyl group to control the stereoselectivity of 1,5-asymmetric induction processes. The use of DIBAL/Yb(OTf)3 or L-Selectride as the reducing agents provides δ-hydroxysulfoxides with the opposite configuration at the hydroxylic carbon in a highly stereoselective way.

Chiral synthesis via organoboranes. 48. Efficient synthesis of trans- fused bicyclic and cyclic ketones and secondary alcohols in high optical purities via asymmetric cyclic hydroboration with isopinocampheylchloroborane etherate

Highly stereo- and enantioselective annelation has been achieved for the synthesis of trans-fused bicyclic and cyclic ketones via the asymmetric cyclic hydroboration of suitable cyclic dienes, such as 1-allyl-1- cycloalkenes or 1-vinyl-1-cycloalkenes and appropriate acyclic 1,4-dienes, respectively, with enantiomerically pure isopinocampheylchloroborane etherate (IpcBHCl·Et2O). The IpcBHCl· Et2O (an 86-90% equilibrium mixture) was readily synthesized by the reaction of an equivalent amount of hydrochloric acid in ethyl ether (Et2O) with optically pure isopinocampheylborane (IpcBH2). The hydroboration of the terminal double bond of a representative diene with IpcBHCl·Et2O readily provided the corresponding isopinocampheylalkylchloroborane (IpcRBCl). Subsequent hydridation of the IpcRBCl with lithium aluminum hydride (LAH, 0.25 equiv) at -20 or -25 °C generated the intermediate isopinocampheylalkylborane (IpcRBH) almost instantly, which then underwent a rapid stereospecific and enantioselective intramolecular cyclic hydroboration to provide the intermediate cyclic trialkylborane. This trialkylborane, on treatment with an aldehyde, liberated the optically pure auxiliary as α-pinene (readily recovered for recycle) to provide the corresponding cyclic borinate ester. This ester reacted smoothly with α,α-dichloromethyl methyl ether (DCME) in the presence of a hindered base (the DCME reaction) to yield, after oxidation with buffered hydrogen peroxide, the trans-fused bicyclic or cyclic ketone in high enantiomeric excess (ee). In another improved approach, in situ generated IpcBHCl·Et2O, from the reduction of isopinocampheyldichloroborane (IpcBCl2) with trimethylsilane (Me3SiH), in the presence of representative dienes in Et2O provided considerably improved optical yields of the bicyclic and cyclic ketones. The trialkylboranes obtained from suitable acyclic dienes can be easily protonolyzed to provide the secondary alcohols in high ee.