29362-79-6Relevant academic research and scientific papers
A general method for the highly diastereoselective, kinetically controlled alkylation of ( )-nopinone
Campos, Kevin R,Lee, Sandra,Journet, Michel,Kowal, Jason J,Cai, Dongwei,Larsen, Robert D,Reider, Paul J
, p. 6957 - 6959 (2007/10/05)
A general method for the monoalkylation of (+)-nopinone was developed for a variety of carbon and heteroatom electrophiles to afford the kinetically controlled product 2 with high diastereoselectivity (98% d.e.) and excellent yield (75-90%).
REACTIONS OF p-TOLUENESULFONIC ACID TERPENE DERIVATIVES WITH LITHIUM IN ETHYLAMINE
Rykowski, Zbigniew,Gubrynowicz, Olaf,Wrzesien, Justyna
, p. 1237 - 1244 (2007/10/02)
Reactions of terpene p-toluenesulfonamides and p-toluenesulfonates with lithium in ethylamine were stated to afford, exclusively or mainly, respective amines and alcohols as the result of N-S or O-S bond cleavage.Presence of hydroxyl groups is not a hindrance. 2α-Hydroxy-3α-tosyloxypinane undergoes, partially, a rearrangement.The mechanism of that reaction is discussed.
Synthesis of Chiral Conformationally Fixed Cyclohexanones
Konopelski, Joseph P.,Djerassi, Carl
, p. 2297 - 2301 (2007/10/02)
Two syntheses of (R)-(+)-2,2-dimethyl-4-tert-butylcyclohexanone (1) are presented.Related 4-alkylcyclohexanones (intermediates in the syntheses) bear other (potential) conformational anchoring groups.The key steps in the syntheses are the opening of the cyclobutane ring of (+)-3,3-dimethylnopinone (10) by either pyrolysis or reaction with BBr3.The high optical purity of the final compound was determined by analysis of the 19F NMR spectrum of the diastereomeric ester mixture obtained from the reaction of alcohol (+)-14b with (S)-(+)-MTPA chloride
Optical Rotary Dispersion Studies. 129. Conformational Isotope Effects and Octant Contributions of CD3 and 13CH3 Groups in Cyclohexanone
Lee, Shy-Fuh,Edgar, Mark,Pak, Ghwang Siek,Barth, Guenter,Djerassi, Carl
, p. 4784 - 4790 (2007/10/02)
Through the variable-temperature circular dichroism measurements of (2S)-2-methyl-d3-2-methylcyclohexanone (3) and (2S)-2-methyl-13C-2-methylcyclohexanone (4), quantitative values for the conformational isotope effect are obtained.The chair conformation with the heavier isotope in the equatorial position is found to be energetically preferred by 3.4 and 1.5 cal/mol for 3 and 4, respectively, and empirical force-field calculations qualitatively confirm this view.The CD3 and 13CH3 groups act as weaker octant perturbers compared to CH3.
