Zajac,W.W. et al.

, p. 1547 - 1550 (1966)

Kleinfelter

, p. 840 (1967)

Traylor,Baker

, p. 2746,2748 (1963)

RHODIUM(I)-CATALYZED ASYMMETRIC HYDROBORATION OF ALKENES WITH 1,3,2-BENZODIOXABOROLE

Sato, Makoto,Miyaura, Norio,Suzuki, Akira

, p. 231 - 234 (1990)

Several rhodium(I) complexes containing chiral phosphine, (+)DIOP, (+)BINAP, (S,S) CHIRAPHOS, and (S)(R)BPPFA, have been found to be effective as catalyst for the asymmetric hydroboration of prochiral alkenes with catecholborane (1,3,2-benzodioxaborole) to give optically active 2-alkyl-1,3,2-benzodioxaboroles. among the ligands examined, DIOP has been recognized to be most effective to give high asymmetric induction.

Loewen et al.

, p. 4059 (1969)

Kwart,Blazer

, p. 2726,2727 (1970)

Asymmetric Functionalization of Bicycloalkenes by Catalytic Enantioposition-Selective Hydrosilylation

Uozumi, Yasuhiro,Lee, Sang-Yong,Hayashi, Tamio

, p. 7185 - 7188 (1992)

Hydrosilylation of norbornene with trichlorosilane in the presence of palladium catalyst (0.01-0.1 mol percent) coordinated with (R)-MOP ligand gave a quantitative yield of exo-2-trichlorosilylnorbornane, which was oxidized with hydrogen peroxide to give (1S,2S,4R)-exo-2-norbornanol in 96percent ee.The similar hydrosilylation and oxidation of endo-5,6-dicarbomethoxy-2-norbornene, bicyclooctene, and norbornadiene gave the corresponding bicyclic alcohols of 94percent ee, 92percent ee, and 95percent ee, respectively.

Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration

Wang, Yong,Cao, Xinyi,Zhao, Leyao,Pi, Chao,Ji, Jingfei,Cui, Xiuling,Wu, Yangjie

supporting information, p. 4119 - 4129 (2020/08/10)

A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).

Potential Synthetic Adaptogens: V. Synthesis of Cage Monoamines by the Schwenk–Papa Reaction

Brunilin, R. V.,Mkrtchyan, A. S.,Nawrozkij, M. B.,Novakov, I. A.,Vernigora, A. A.,Voloboev, S. N.,Vostrikova, O. V.

, p. 1742 - 1748 (2020/01/11)

The reduction of cage ketoximes under Schwenk–Papa reaction conditions was studied to establish that the d,l, d- and l-camphor oximes are smoothly reduced to the corresponding amines in high yields. At the same time, d,l-norcamphor and adamantan-2-one oximes undergo partial catalytic deoximation to form a mixture of the corresponding amines and alcohols.