Lanthanide-Catalyzed Reversible Alkynyl Exchange by Carbon-Carbon Single-Bond Cleavage Assisted by a Secondary Amino Group

2016 ◽  
Vol 128 (38) ◽  
pp. 11657-11661 ◽  
Author(s):  
Yinlin Shao ◽  
Fangjun Zhang ◽  
Jie Zhang ◽  
Xigeng Zhou
Keyword(s):  
Bond Cleavage ◽  
Amino Group ◽  
Single Bond ◽  
Secondary Amino

Rh(iii)-Catalyzed Csp2–Csp3 bond alkoxylation of α-indolyl alcohols via C–C σ bond cleavage

2021 ◽  
Author(s):  
Can Yang ◽  
Zhipeng Liu ◽  
Xinwei Hu ◽  
Haisheng Xie ◽  
Huanfeng Jiang ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Single Bond ◽  
Sigma Bond

A Rh(iii)-catalyzed direct Csp2–Csp3 bond alkoxylation of α-(2-indolyl)alcohols with alcohols has been achieved via C–C sigma bond/C–O single bond switch.

Amino Acid Salt Catalyzed Asymmetric Addition Reaction of Acetylacetone to Maleimides and 2-(2-Oxoindolin-3-ylidene)malononitriles

Synlett ◽  
2019 ◽  
Vol 30 (10) ◽  
pp. 1241-1245 ◽  
Author(s):  
Haiyan Wu ◽  
Hongxin Liu ◽  
Juan Li ◽  
Xinhua Li ◽  
Hong-Ping Xiao ◽  
...  
Keyword(s):  
Amino Acid ◽  
Addition Reaction ◽  
Optical Purity ◽  
Activation Mechanism ◽  
Amino Group ◽  
Acid Salt ◽  
Natural Amino Acid ◽  
Catalytic Potential ◽  
Amino Acid Salt ◽  
Secondary Amino

The exploration of catalytic potential of natural amino acid salt in activation of 1,3-dicarbonyls was carried out, in which maleimides and 2-(2-oxoindolin-3-ylidene)malononitriles were found to be good electrophiles and afforded the desired products with excellent yield and moderate optical purity. Control experiments showed that the secondary amino group of barium (S)-prolinate is critical to the catalytic activity as well as enantiocontrol, thus revealed an enamine activation mechanism is possible in the present methodology.

Cu(I)-Catalyzed Intramolecular Hydroamination of Unactivated Alkenes Bearing a Primary or Secondary Amino Group in Alcoholic Solvents

2009 ◽  
Vol 11 (10) ◽  
pp. 2145-2147 ◽  
Author(s):  
Hirohisa Ohmiya ◽  
Toshimitsu Moriya ◽  
Masaya Sawamura
Keyword(s):  
Amino Group ◽  
Secondary Amino

Metal derivatives of amide oximes. III. Products of the reaction between dialkyldichlorosilanes and amide oximes

1974 ◽  
Vol 27 (11) ◽  
pp. 2319 ◽  
Author(s):  
AB Goel ◽  
VD Gupta
Keyword(s):  
Infrared Spectra ◽  
Amino Group ◽  
Monomeric Form ◽  
Metal Derivatives ◽  
Secondary Amino ◽  
Derivatives Of

The reaction of dialkyldichlorosilanes with amide oximes leads to cyclic products whose monomeric form has an l-oxa-3,5-diaza-2-silacyclopent-4-ene structure. These compounds exist mostly in adimeric form, occasionally monomeric or trimeric. Their infrared spectra have been interpreted. The secondary amino group of the compounds has been trisilylated.

ANNOTININE: THE REACTIONS OF THE CYCLIC ETHER FUNCTION

1954 ◽  
Vol 32 (3) ◽  
pp. 268-279 ◽  
Author(s):  
H. L. Meier ◽  
P. D. Meister ◽  
Léo Marion
Keyword(s):  
Chromic Acid ◽  
Cyclic Ether ◽  
The Other ◽  
Amino Group ◽  
Imino Group ◽  
Unsaturated Lactone ◽  
Clemmensen Reduction ◽  
Secondary Amino ◽  
Concentrated Solution ◽  
Chromous Chloride

Treatment of annotinine chlorohydrin with chromous chloride has been found to produce not only the already reported unsaturated lactone A (C16H21O2N), but also a second unsaturated lactone B (C16H21(23)O2N), and a hydroxylactone (C16H23O3N). Under the action of a concentrated solution of the same reagent the hydroxylactone is converted to the unsaturated lactone B. On hydrogenation the latter gives a dihydrolactone B which seems to contain a secondary amino group. Annotinine hydrate on treatment with thionyl chloride gives an unsaturated chlorolactone (C16H20O2NCl) which can be hydrogenated and subsequently dechlorinated to produce a third lactone C, different from either of dihydrolactones A or B, but which like the latter seems to contain an imino group. Oxidation of annotinine hydrate with chromic acid produces a hydroxyketone which can be converted into an oxime and, therefore, one of the hydroxyls of the hydrate is secondary while the other is probably tertiary. On the other hand, oxidation of annotinine with potassium permanganate gives rise to a lactam which by the Clemmensen reduction is converted to a mixture of lactam chlorohydrin and dihydrolactone A.

scholarly journals Oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′-diamines (BINAMs) via C–C bond cleavage and nitrogen migration: a versatile synthesis of U-shaped azaacenes

2014 ◽  
Vol 50 (71) ◽  
pp. 10291-10294 ◽  
Author(s):  
Youhei Takeda ◽  
Masato Okazaki ◽  
Satoshi Minakata
Keyword(s):  
Bond Cleavage ◽  
Single Bond ◽  
Skeletal Rearrangement

An oxidative skeletal rearrangement of 1,1′-binaphthalene-2,2′-diamines (BINAMs) that involves the cleavage of a strong C–C single bond of the binaphthalene unit and the nitrogen migration has been discovered.

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