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2.1.1.4.1 Catalytic Asymmetric Michael Reactions

DOI: 10.1055/sos-SD-205-00001

Nagasawa, K.; Sohtome, Y.Science of Synthesis: Asymmetric Organocatalysis, (2012220.

Catalytic asymmetric 1,4-addition (Michael) reactions are useful tools for the preparation of nitrogen-containing chiral building blocks.[‌28‌‌30‌] Among the currently available methods, asymmetric organocatalytic conjugate additions to nitroalkenes have received great attention as a result of their reactivity and versatility. In 2006, Terada and co-workers reported the results of their initial studies leading to the development of the axially chiral guanidine catalyst (R)-53 (Scheme 20) for catalytic asymmetric Michael reactions of 1,3-dicarbonyl compounds 55 with nitroalkenes 54 to give products 56.[‌6‌,‌31‌]

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Meeeeeeeeee 88

M8 M8 M8 M8 88 (eee%) Meeeeee Meee (e) Meeee (%) ee (%) Mee
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Me MMe MMe M 8 Me8M 8 88 88 [‌88‌]
Me MeMe MeMe M 8 Me8M 8 88 88 [‌88‌]
8-MeMM8M8 MMe MMe M 8 Me8M 8 88 88 [‌88‌]
8-MeM8M8 MMe MMe M 8 Me8M 8 88 88 [‌88‌]
8-M8MM8M8 MMe MMe M 8 Me8M 8 88 88 [‌88‌]
8-MeMM8M8 MMe MMe M 8 Me8M 8 88 88 [‌88‌]
8-MeM8M8 MMe MMe M 8 Me8M 8 88 88 [‌88‌]
8-MeMM8M8 MMe MMe M 8 Me8M 8 88 88 [‌88‌]
8-MeM8M8 MMe MMe M 8 Me8M 8 88 88 [‌88‌]
8-MeM8M8 MMe MMe M 8 Me8M 8 88 88 [‌88‌]
8-eeeee MMe MMe M 8 Me8M 8 88 88 [‌88‌]
8-eeeeeeee MMe MMe M 8 Me8M 8 88 88 [‌88‌]
eMe MMe MMe M 8 eMe8M 88 88 88 [‌88‌]
eMe MMe MMe M 8 eMe8M 88 88 88 [‌88‌]
Me MMe MMe M 8 eMe8M 88 88 88 [‌88‌]
Me MMe MMe Me 8 Me8M 88 88 88 [‌88‌]
Me Me Me M 8 Me8M 8 88 88 [‌88‌]
Me Me MMe M 8 eMe8M 8 88 88e [‌88‌]

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Meeeeeeeeeee Meeeeeeee

Meeeeeee 8-(8-Meeee-8-eeeeeeeeeee)eeeeeeee (88, M8=Me; M8=M8=MMe; M8=M); Meeeeee Meeeeeeee:[‌88‌]

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References


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