Highly Stereoselective Synthesis of Substituted Prolyl Peptides Using a Combination of Biocatalytic Desymmetrization and Multicomponent Reactions

Znabet, Anass; Ruijter, Eelco; Kanter, Frans J. J. de; Köhler, Valentin; Helliwell, Madeleine; Turner, Nicholas J.; Orru, Romano V. A.

doi:10.1002/anie.201001592

Cited by 116 publications

(89 citation statements)

References 37 publications

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“…Oxidative desymmetrization of meso-pyrrolidines by monoamine oxidase N (MAO-N) from Aspergillus niger and subsequent Ugitype MCR in the synthesis of organocatalysts (e.g. 125), [100] synthetic alkaloids (e.g. 126), [103] and the hepatitis C drug candidate telaprevir (124).…”

Section: Discussionmentioning

confidence: 99%

“…Recently, we used a monoamine oxidase to desymmetrize meso-pyrrolidines to the corresponding 1-pyrrolines, which then react in a highly diastereoselective Ugi-type MCR (Scheme 15). [100] Moreover, we were able to exploit this method in a short and efficient asymmetric synthesis of the important hepatitis C drug candidate (HCV NS3 protease inhibitor) telaprevir (124), [101] as well as a Wennemers-type organocatalyst for asymmetric Henry reactions (125) [100,102] and polycyclic alkaloid-type compounds (e.g. 126).…”

Section: Towards Stereoselective Mcrsmentioning

confidence: 99%

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Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity

2011

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Multicomponent reactions have become increasingly popular as tools for the rapid generation of small-molecule libraries. However, to ensure sufficient molecular diversity and complexity, there is a continuous need for novel reactions. Although serendipity has always played an important role in the discovery of novel (multicomponent) reactions, rational design strategies have become much more important over the past decade. In this Review, we present an overview of general strategies that allow the design of novel multicomponent reactions. The challenges and opportunities for the future will be discussed.

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Section: Discussionmentioning

confidence: 99%

Section: Towards Stereoselective Mcrsmentioning

confidence: 99%

Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity

2011

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“…TheM AO-Nderived D 1 -pyrrolines have also been embedded into multicomponent reactions such as the Ugi reaction (Scheme 36 a). [133] Very recently,t he further chemical oxidation of MAO-N-derived imines into lactams was demonstrated (Scheme 36 b). [134] Similarly,C hen and co-workers reported awhole-cell oxidation of some amines to lactams.…”

Section: Oxidation Of Aminesmentioning

confidence: 99%

Biocatalytic Oxidation Reactions: A Chemist's Perspective

et al. 2018

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Oxidation chemistry using enzymes is approaching maturity and practical applicability in organic synthesis. Oxidoreductases (enzymes catalysing redox reactions) enable chemists to perform highly selective and efficient transformations ranging from simple alcohol oxidations to stereoselective halogenations of non‐activated C−H bonds. For many of these reactions, no “classical” chemical counterpart is known. Hence oxidoreductases open up shorter synthesis routes based on a more direct access to the target products. The generally very mild reaction conditions may also reduce the environmental impact of biocatalytic reactions compared to classical counterparts. In this Review, we critically summarise the most important recent developments in the field of biocatalytic oxidation chemistry and identify the most pressing bottlenecks as well as promising solutions.

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“…However, good diastereoselectivity has been obtained so far only with a few types of chiral substrates [9–15]. In most cases these are represented by five-membered imines (pyrrolines) with a stereogenic centre α to the imine carbon (1,2-induction), although this relative arrangement is not a guarantee of good stereoselectivity [8,14,16].…”

Section: Introductionmentioning

confidence: 99%

Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines

Banfi¹,

Basso²,

Cerulli³

et al. 2011

Beilstein J. Org. Chem.

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SummaryThe Ugi reaction of 2-substituted dihydrobenzoxazepines was found to proceed with unexpectedly good diastereoselectivitiy (diastereoisomeric ratios up to 9:1), despite the large distance between the pre-existing stereogenic centre and the newly generated one. This result represents the first good 1,4 asymmetric induction in an Ugi reaction as well as the first example of diastereoselective Ugi reaction of seven membered cyclic imines. It allows the diversity-oriented synthesis of various tetrahydro[f][1,4]benzoxazepines.

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Highly Stereoselective Synthesis of Substituted Prolyl Peptides Using a Combination of Biocatalytic Desymmetrization and Multicomponent Reactions

Cited by 116 publications

References 37 publications

Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity

Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity

Biocatalytic Oxidation Reactions: A Chemist's Perspective

Long-range diastereoselectivity in Ugi reactions of 2-substituted dihydrobenzoxazepines

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