Journal Article 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

7pp.3791 - 3797 , 2016-02-22 , Royal Society of Chemistry
ISSN:2041-6539
Description
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.
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