109949-95-3Relevant academic research and scientific papers
Palladium-Catalyzed Umpolung Type-II Cyclization of Allylic Carbonate-Aldehydes Leading to 3-Methylenecycloalkanol Derivatives
Tsukamoto, Hirokazu,Kawase, Ayumu,Doi, Takayuki
supporting information, p. 3733 - 3738 (2019/07/17)
Palladium-catalyzed umpolung type-II cyclization of allylic carbonate-aldehydes leading to 3-methylenecycloalkanol derivatives was developed. The formate reductant was effective for the cyclization without causing a reduction of the η3-allylpalladium intermediate. One-pot decarboxylative allylation of aldehyde-containing malonate with 2-[(acetyloxy)methyl]-2-propenyl methyl carbonate followed by the cyclization of the allyl acetate-aldehyde formed in situ was also achieved. The high diastereoselectivities observed in the cyclization of branched substrates indicates that a chair-chair transition state should be involved. Based on the presumed transition state, we could predict the enantioselectivity of the cyclization using SEGPHOS as a chiral diphosphine ligand and obtain optically active alcohols in up to 95:5 er. (Figure presented.).
Electroorganic chemistry. 120. New patterns of anodic oxidation of amides. Synthesis of α-amino aldehyde acetals and pyrrolidines from amines
Shono, Tatsuya,Matsumura, Yoshihiro,Katoh, Susumu,Takeuchi, Kei,Sasaki, Katsushi,Kamada, Tohru,Shimizu, Rie
, p. 2368 - 2372 (2007/10/02)
Anodic oxidation of N-alkyltosylamides 1 in methanol containing KX (X = Br, I) gave two types of products, α-(tosylamino) aldehyde acetals 2 and pyrrolidine derivatives 3, and each of the products could selectively be formed by modifying the reaction conditions when the alkyl group on the nitrogen of 1 was not branched at its α-position. Namely, anodic oxidation ot N-(α-unbranched alkyl)tosylamides 1a-g in methanol containing NaOMe and KI at -10°C followed by further anodic oxidation at 25°C afforded 2 in good yields, while that of 1 in a two-layer system consisting of cyclohexane and water containing KOH and KBr under heating yielded solely 3. On the other hand, N-(α-branched alkyl)tosylamides 1h-j gave always 3. Two types of reaction routes leading to each of the products were proposed.
ELECTROOXIDATIVE REARRANGEMENT OF TOSYLAMINO GROUP: FACILE SYNTHESIS OF α-AMINO ALDEHYDES FROM PRIMARY AMINES
Shono, Tatsuya,Matsumura, Yoshihiro,Katoh, Susumu,Inoue, Kenji,Matsumoto, Yonetatsu
, p. 6083 - 6086 (2007/10/02)
Anodic axidation of primary N-tosylamines in methanol containing halide ion gave α-(N-tosylamino) aldehyde dimethyl acetals, synthetically useful intermediates equivalent to α-amino aldehydes.
