Catalytic discrimination between formyl groups in regio- and stereoselective intramolecular cross-aldol reactions

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 t...

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Published inChemical science (Cambridge) Vol. 7; no. 6; pp. 3791 - 3797
Main Authors Baba, Tomonori, Yamamoto, Junya, Hayashi, Kazuhiro, Sato, Makoto, Yamanaka, Masahiro, Kawabata, Takeo, Furuta, Takumi
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2016
Subjects
Amines
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Dials
Discrimination
Isotope effect
Physical Sciences
Reaction kinetics
Science & Technology
Stereoselectivity
COMPLEX
DIELS-ALDER REACTION
ALPHA-ACYLOXYACROLEINS
ORGANOCATALYSIS
ENOLIZABLE ALDEHYDES
DERIVATIVES
CHIRAL AMINO-ACID
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Summary: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.
Bibliography:KAKEN
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ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc04594k