38313-10-9

Upstream product

• 1074-26-6 4,4-dimethyl-2,3-epoxycyclohexanone 
• 6553-64-6 6,6-Dimethyl-2-cyclohexen-1-one 
• 1073-13-8 4,4-dimethylcyclohexenone 
• 1272341-16-8 C₁₆H₂₄OSi 

Downstream Products

• 80663-73-6 (+/-)-6,6-dimethylcyclohex-2-en-1-yl acetate 
• 1239277-49-6 6,6-dimethylcyclohex-2-en-1-yl acetate 
• 80663-74-7 Acetic acid (1S,5S,6S)-5-chloro-2,2-dimethyl-6-phenylselanyl-cyclohexyl ester 
• 80663-78-1 Acetic acid 3-chloro-6,6-dimethyl-cyclohex-2-enyl ester 
• 1073-13-8 4,4-dimethylcyclohexenone 
• 6553-64-6 6,6-Dimethyl-2-cyclohexen-1-one 

Relevant academic research and scientific papers

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.

Enzymatic resolution of racemic secondary cyclic allylic alcohols

The resolutions of five racemic cyclic alcohols: 6,6-dimethylcyclohex-2-en-1-ol (±)-5, 4,4-dimethylcyclohex-2-en-1-ol (±)-7, 5,5-dimethylcyclohex-2-en-1-ol (±)-11 and isomeric trans-(±)-13 and cis-piperitols (±)-14 are presented. They were resolved by enzymatic esterification with vinyl esters or by enzymatic hydrolysis of their racemic esters in phosphate buffer. The following lipases were used as biocatalysts: Novozyme 435 (Candida antarctica), Amano PS (Burkholderia cepacia) and lipase from Candida cylindracea. All isomers of alcohols were obtained with at least 96% ee.

Origins of Regio- and Stereoselectivity in Additions of Phenylselenenyl Chloride to Allylic Alcohols and the Applicability of These Additions to a Simple 1,3-Enone Transposition Sequence

The regio- and stereoselectivity of phenylselenenyl chloride additions to allylic alcohols and their derivatives have been systematically studied.On the basis of the results, a mechanism involving two basic premises is proposed.These are as follows: (a) allylic oxygen's direct selenonium ion formation to the syn face of the double bond; (b) axial attack of the chloride ion is kinetically favored over equatorial attack.A series of rules which are useful for predicting the regio- and stereoselectivity of phenylselenenyl chloride additions to allylic systems are discussed.In addition, these reactions can be used as the key step in a general 1,3-enone transposition sequence.Several examples of this transposition sequence are illustrated.