6965-77-1Relevant academic research and scientific papers
Catalytic discrimination between formyl groups in regio-and stereoselective intramolecular cross-Aldol reactions
Baba, Tomonori,Yamamoto, Junya,Hayashi, Kazuhiro,Sato, Makoto,Yamanaka, Masahiro,Kawabata, Takeo,Furuta, Takumi
, p. 3791 - 3797 (2016/06/09)
Catalytic discrimination between inequivalent formyl groups was achieved using an aniline-Type acid-base catalyst for the regio-, diastereo-, and enantioselective intramolecular cross-Aldol reactions of enolizable dials. Although l-proline gave a mixture of the regio-and stereoisomeric products in the presence of an N-containing 1,6-dial, the aniline-Type catalyst afforded anti-3,4-disubstituted pyrrolidine in high regio-, and stereoselectivity beyond the background reaction, which led to the regioisomeric 2,3-disubstituted products. The mild reactivity of the aniline-Type amine facilitated catalytic discrimination between the inequivalent formyl groups. Kinetic isotope effect studies and reductive amination experiments suggested that the regioselectivity was controlled under the enamine-forming steps.
A Convenient Synthesis of 1,3,6-Dioxazocine, 1,3,7-Dioxazocine, 1,3,8-Dioxazecine and 1,3-Dioxa-6,10-diazadodecane
Krakowiak, Krzysztof E.,Kotelko, Barbara,Bradshaw, Jerald S.,Dalley, N. Kent
, p. 1327 - 1330 (2007/10/02)
A series of perhydro heterocycles of eight to ten ring members containing one nitrogen and two oxygen atoms has been prepared.These include four 1,3,6-dioxazocines, and 1,3,7-dioxazonine and one 1,3,8-dioxazecine.A twelve-membered ring containing two oxygen and two nitrogen atoms was also prepared.An X-ray structure of one of the 1,3,6-dioxazocines, 5, was determined.This compound crystallized in the orthorhomic space group Pccn with a = 25.922(15) Angstroem, b = 12.150(4) Angstroem and C = 9.342(4) Angstroem.Two of the 1,3,6-dioxazocines have the benzylidine acetal structure which will hydrolyze to give benzaldehyde.
