New Strategies for Organic Catalysis:  The First Enantioselective Organocatalytic 1,3-Dipolar Cycloaddition

Jen, Wendy S.; Wiener, John J. M.; MacMillan, David W. C.

doi:10.1021/ja005517p

Cited by 508 publications

(211 citation statements)

References 3 publications

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“…This catalysis concept was founded on the mechanistic hypothesis that the reversible formation of iminium ions from ␣,␤-unsaturated aldehydes and amines (Scheme 2) might emulate the equilibrium dynamics and -orbital electronics that are inherent to Lewis acid catalysis (Scheme 1). This new catalysis strategy has subsequently been applied to the development of a variety of enantioselective chemical processes, including cycloadditions (46,47,50), Mukaiyama-Michael additions (53), Friedel-Crafts alkylations (48,49,52), heteroconjugate additions, hydrogenations, and cascade reactions.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition–cyclization strategy: Synthesis of (–)-flustramine B

Austin

Kim

Sinz

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

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442

117

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Pyrroloindoline and bispyrroloindoline are a subclass of alkaloid structural motifs that commonly exhibit biological activity. An enantioselective organocatalytic approach to the synthesis of pyrroloindoline architecture is described. The addition-cyclization of tryptamines with ␣,␤-unsaturated aldehydes in the presence of imidazolidinone catalysts 1 and 8 provides pyrroloindoline adducts in high yield and excellent enantioselectivities. This transformation is successful for a wide range of tryptamine and ␣,␤-unsaturated aldehyde substrates. This amine-catalyzed sequence has been extended to the enantioselective construction of furanoindoline frameworks. Application of this pyrroloindoline-forming reaction to natural product synthesis has been accomplished in the context of the enantioselective synthesis of (؊)-flustramine B.

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Section: Methodsmentioning

confidence: 99%

Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition–cyclization strategy: Synthesis of (–)-flustramine B

Austin

Kim

Sinz

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

442

117

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“…Since the first report by MacMillan using nitrones, 74 the range of suitable dipoles for organocatalytic processes has been significantly broadened.…”

Section: Organocatalytic Proceduresmentioning

confidence: 99%

Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides

2014

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Catalytic asymmetric 1,3-dipolar cycloadditions of azomethine ylides have turned out to be one of the most efficient methods for the preparation of enantioenriched pyrrolidines. The past decade has witnessed the development of a bunch of well-defined catalytic systems capable of affording excellent diastereo and enantioselectivities. Recently, a great effort has been focused on expanding the scope of the cycloaddition with regard to both reaction partners. In this review,

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“…The word Organocatalysis has been introduced in the scientific community in 2000 by MacMillan, one of the pioneers of the field [13,14]. Organocatalysis refers to the use of small organic molecules to catalyse organic transformations.…”

Section: Definition and Origins Of Organocatalysismentioning

confidence: 99%

Organocatalysts for enantioselective synthesis of fine chemicals: definitions, trends and developments

Federsel¹

2014

ScienceOpen Research

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Organocatalysis, that is the use of small organic molecules to catalyse organic transformations, has been included among the most successful concepts in asymmetric catalysis and it has been used for the enantioselective construction of C-C, C-N, C-O, C-S, C-P, and C-halide bonds. Since the seminal works in early 2000, the scientific community has been paying an ever-growing attention to the use of organocatalysts for the synthesis, with high yields and remarkable stereoselectivities, of optically active fine chemicals of interest for the pharmaceutical industry. A brief overview is here presented about the two main classes of substrate activation by the catalyst: covalent organocatalysis and non-covalent organocatalysis, with a more stringent focus on some recent outcomes in the field of the latter and of hydrogen-bond-based catalysis. Finally, some successful examples of heterogenisation of organocatalysts are also discussed, in the view of a potential industrial exploitation.

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New Strategies for Organic Catalysis: The First Enantioselective Organocatalytic 1,3-Dipolar Cycloaddition

Cited by 508 publications

References 3 publications

Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition–cyclization strategy: Synthesis of (–)-flustramine B

Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition–cyclization strategy: Synthesis of (–)-flustramine B

Recent advances in the catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides

Organocatalysts for enantioselective synthesis of fine chemicals: definitions, trends and developments

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