62327-74-6

Upstream product

• 853065-81-3 1-methylgeraniol 
• 106-26-3 cis-3,7-dimethyl-2,6-octadienal 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 67845-50-5 8-hydroxy-2,6-dimethyl-nona-2,6-diene 
• 129454-75-7 4,8-dimethyl-3,4-epoxy-7-nonen-2-ol 
• 129454-75-7 1-[(2S,3R)-3-Methyl-3-(4-methyl-pent-3-enyl)-oxiranyl]-ethanol 
• 817-88-9 4,8-dimethyl-3,7-nonadien-2-one 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 129454-75-7 trans-3,4-epoxy-4,8-dimethyl-7-nonen-2-ol 

Relevant academic research and scientific papers

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Photochemical Reactions Photochemistry of Acylsilanes: Photolyses and Thermolyses of α,β-Epoxy Silyl Ketones

The photolyses and thermolyses of the α,β-epoxy silyl ketones 5 and 6 are described.On n,?*-excitation, the silyl ketones 5 and 6 were transformed to the ketone 7 and the ketene 8 in quantitative yield.The formation of 8 may be explained by initial cleavage of the C(α)-O bond and subsequent C(1) -> C(2) migration of the (t-Bu)Me2Si group.In contrast to the acylsilanes 5 and 6, the photolyses of the analogous methyl ketones 11 and 12 gave a very complex mixture of products.On thermolysis, 5 and 6 yielded the ketone 7 and the acetylenic compound 9, which were probably formed via a siloxycarbene intermediate.In addition, the 1,3- dioxole 10 was formed via an initial C(α)-C(β) bond cleavage leading to the ylide g and subsequent intramolecular addition of the carbonyl group.The analogous 1,3-dioxole 13 was obtained on pyrolysis of the methyl ketones 11 and 12.

The reaction of trialkylstannylmethyllithium with α,β-epoxy ketones and α-chloro ketones

The reactions of trialkylstannylmethyllithium with α,β-epoxy ketones afforded mainly cyclopropanols, while α-chloro ketones afforded allyl alcohols and/or cyclopropanols, in varying amounts depending upon the molar ratio of the reagent to the substrate.