Highly Efficient Asymmetric Michael Reaction of Aldehydes to Nitroalkenes with Diphenylperhydroindolinol Silyl Ethers as Organocatalysts

New dihydroindole and perhydroindole derivatives were synthesized in good yields and evaluated as chiral catalysts in the asymmetric Michael reaction of aldehydes to nitroalkenes. (2S,3aS,7aS)‐Diphenylperhydroindolinol silyl ether 10 facilitated the reaction of a wide range of aldehyde and nitroalke...

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Published inAdvanced synthesis & catalysis Vol. 351; no. 14-15; pp. 2449 - 2459
Main Authors Luo, Ren-Shi, Weng, Jiang, Ai, Hui-Bing, Lu, Gui, Chan, Albert S. C.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.10.2009
WILEY‐VCH Verlag
Wiley
Subjects
asymmetric catalysis
Chemistry
Chemistry, Applied
Chemistry, Organic
Michael addition
nitroalkenes
organocatalysis
perhydroindolinols
Physical Sciences
Science & Technology
Michael addition
nitroalkenes
ALDOL
ACID
perhydroindolinols
asymmetric catalysis
CHIRAL LITHIUM AMIDE
ALPHA,ALPHA-DISUBSTITUTED ALDEHYDES
organocatalysis
BETA-AMINO ALCOHOLS
KETONES
NITROOLEFINS
PROLINE
DERIVATIVES
CONJUGATE ADDITION
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Summary:New dihydroindole and perhydroindole derivatives were synthesized in good yields and evaluated as chiral catalysts in the asymmetric Michael reaction of aldehydes to nitroalkenes. (2S,3aS,7aS)‐Diphenylperhydroindolinol silyl ether 10 facilitated the reaction of a wide range of aldehyde and nitroalkene substrates, providing Michael adducts in nearly optically pure form (99% ee), good yields and high diastereoselectivities (syn/anti up to 99:1). These results show for the first time that perhydroindole derivatives can also be highly efficient organocatalysts for the asymmetric Michael reaction, exhibiting comparable or even better enantioselectivities than proline derivatives.
Bibliography:Scientific Research Foundation for the Returned Overseas Chinese Scholars
State Education Ministry of China
European Commission - No. FP7-201431 (CATAFLU.OR)
istex:E692D851E963800665EA345596E2988A47CE358D
Program for New Century Excellent Talents in University
ArticleID:ADSC200900355
ark:/67375/WNG-Q7XLQB75-9
ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900355