Selective Formation of α-Methylene-β-amino acid Derivatives through the Aza Version of the Baylis−Hillman Reaction

Balan, Daniela; Adolfsson, Hans

doi:10.1021/jo0158635

Cited by 65 publications

(31 citation statements)

References 28 publications

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“…Having successfully developed a one-pot, threecomponent aza-MBH reaction [29,30], they implemented enantioselectivity in their protocol by replacing DABCO with cinchona derivatives [31]. N-Sulfonyl imines, formed in situ from tosylamide and an aldehyde (in the presence of a small amount of titanium 2-propoxide and molecular sieves), reacted with methyl acrylate in the presence of -ICD (4, 15 mol%) to yield the aza-MBH adducts in variable yields (12% 95%) and with moderate enantiomeric excesses (49% 74% ee).…”

Section: Methodsmentioning

confidence: 99%

Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction

Wei

Shi

2010

Chin. Sci. Bull.

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In the past decade, the asymmetric Morita-Baylis-Hillman (MBH)/aza-Morita-Baylis-Hillman (aza-MBH) reaction has attracted great attention because it leads to the formation of densely functionalized products in a catalytic and atom-economic way. The MBH/aza-MBH adducts can be further applied in a wide variety of organic synthesis, such as peptide synthesis and heterocyclic compounds synthesis. After a lot of attempts to improve the enantioselectivity, many types of chiral organocatalysts have been identified as highly enantioselective organocatalysts in MBH/aza-MBH reaction. Especially, certain "privileged chiral catalysts" are highly enantioselective in MBH/aza-MBH reaction, which are designed and developed through introducing bi-/multi-functional groups on the so-called "privileged structures" such as cinchona alkaloids, BINAP/BINOL. This review summarizes the exciting advances about the design and development of chiral catalysts derived from "privileged structures" and their applications in asymmetric MBH/aza-MBH reaction. Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction, privileged chiral catalysts, organocatalysts, chiral amines, chiral phosphines Citation:Wei Y, Shi M. Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction.

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Section: Methodsmentioning

confidence: 99%

Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction

Wei

Shi

2010

Chin. Sci. Bull.

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“…In 2001, Adolfsson and Balan described a three-component reaction with activated alkenes, aldehydes, and tosylamines. [26] In the presence of DABCO or 3-HQD as catalyst, together with La(OTf) 3 and molecular sieves, the aza adducts 25 were obtained in moderate to high yields, along with some alcohol adducts 26 (Scheme 23). Subsequently, they found that use of Ti(OiPr) 4 as the Lewis acid co-catalyst was superior to that of La(OTf) 3 , giving better chemoselectivity in the aza adducts 3.…”

Section: Multicomponent One-pot Reactionsmentioning

confidence: 99%

Aza‐Baylis–Hillman Reactions and Their Synthetic Applications

Shi

2007

Eur J Org Chem

242

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“…Having successfully developed a one-pot, three-component aza-Baylis-Hillman reaction, [25] Balan and Adolfsson implemented enantioselectivity in their protocol by replacing 1,4-diazabicyclo[2.2.2]octane (DABCO) with cinchona derivatives. [26] N-Sulfonyl imines, formed in situ from tosylamide and an aldehyde (in the presence of a small amount of titanium 2-propoxide and molecular sieves), reacted with methyl acrylate in the presence of b-ICPD (15 mol %) to yield the aza-Baylis-Hillman adducts in variable yields (12-95 %) and with moderate enantiomeric excesses (49-74 % ee).…”

Section: Angewandte Chemiementioning

confidence: 99%

Cupreines and Cupreidines: An Emerging Class of Bifunctional Cinchona Organocatalysts

2006

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In the steadily expanding field of organocatalysis, cinchona alkaloids play a prominent role. Until the late 1990s, bifunctional catalysts based on this scaffold relied exclusively on the C9-hydroxy group as the hydrogen-bond donor. Recently, new cinchona catalysts have been developed that feature a phenolic OH group in the C6' position-a structural feature that allows a diverse set of reactions to be catalyzed in a highly stereoselective fashion. This Minireview describes the scope and modes of action of this new class of asymmetric bifunctional organocatalysts.

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Selective Formation of α-Methylene-β-amino acid Derivatives through the Aza Version of the Baylis−Hillman Reaction

Cited by 65 publications

References 28 publications

Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction

Privileged chiral catalysts in asymmetric Morita-Baylis-Hillman/aza-Morita-Baylis-Hillman reaction

Aza‐Baylis–Hillman Reactions and Their Synthetic Applications

Cupreines and Cupreidines: An Emerging Class of Bifunctional Cinchona Organocatalysts

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