56782-80-0Relevant academic research and scientific papers
Atom-Economical Dimerization Strategy by the Rhodium-Catalyzed Addition of Carboxylic Acids to Allenes: Protecting-Group-Free Synthesis of Clavosolide A and Late-Stage Modification
Haydl, Alexander M.,Breit, Bernhard
supporting information, p. 15530 - 15534 (2016/01/26)
Natural products of polyketide origin with a high level of symmetry, in particular C2-symmetric diolides as a special macrolactone-based product class, often possess a broad spectrum of biological activity. An efficient route to this important
Asymmetric chiral ligand-directed alkene dioxygenation
Neufeldt, Sharon R.,Sanford, Melanie S.
supporting information, p. 46 - 49 (2013/04/10)
A Pd-catalyzed asymmetric alkene 1,2-dioxygenation reaction is described. The diastereoselectivity of the reaction is controlled by tethering a chiral oxime ether directing group to the alkene substrate. The best selectivities are obtained with 8-substituted menthone-derived oxime ether auxiliaries.
Pd-catalyzed asymmetric β-hydride elimination en route to chiral allenes
Crouch, Ian T.,Neff, Robynne K.,Frantz, Doug E.
supporting information, p. 4970 - 4973 (2013/06/04)
We wish to report our preliminary results on the discovery and development of a catalytic, asymmetric β-hydride elimination from vinyl Pd(II)-complexes derived from enol triflates to access chiral allenes. To achieve this, we developed a class of chiral p
Copper-Catalyzed Conjugate Addition of Trimethylaluminium to α,β-Unsaturated Ketones
Kabbara, Jazid,Flemming, Steffen,Nickisch, Klaus,Neh, Harribert,Westermann, Juergen
, p. 1489 - 1494 (2007/10/02)
The conjugate methylation of α,β-unsaturated ketones with trimethylaluminium occurs smoothly in a very simple procedure under the catalytic CuI salts.Scope and limitations of this process as well as the influence of solvent and catalyst on the kinetics were studied.In addition, the effect of chlorotrimethylsilane as an additive was investigated.Attack on the carbonyl group in 1,2-fashion could not be observed under the reaction conditions.- Key Words: Conjugate alkylation / Trimethylaluminium / Copper catalysis
Stereochemistry of Addition of Allyl Grignard Reagents to (R)-(+)-Pulegone and Other α,β-Ethylenic Ketones
Idrissi, Mostafa El,Santelli, Maurice
, p. 1010 - 1016 (2007/10/02)
The 1,2-addition of allyl, crotyl, and 2-methyl-2-butenyl Grignard reagents to (R)-(+)-pulegone is regio- and stereoselective.In contrast 3-penten-2-yl and 3-methyl-2-butenyl Grignard reagents undergo 1,2- and 1,4-additions.A "compact approach" stabilized by orbital interaction is the proposed mechanism.A further confirmation was obtained with acyclic enones.
Auxiliary Structure and Asymmetric Induction in the Ene Reactions of Chiral Glyoxylates
Whitesell, James K.,Lawrence, Robert M.,Chen, Huang-Hsing
, p. 4779 - 4784 (2007/10/02)
A variety of chiral auxiliares (1a-13a) were prepared and tested for levels of asymmetric induction control in the ene reaction of chiral glyoxylates.Structural features required for high levels of control were defined by systematic modification of the auxiliary, providing systems with induction levels that ranged from 1.2 to 1 to better than 99.9 to 0.1.
