Catalyst‐Controlled Multicomponent Aziridination of Chiral Aldehydes

Mukherjee, Madhumita; Zhou, Yubai; Dai, Yijing; Gupta, Ani L K; Pulgam, V. Reddy; Staples, Richard J.; Wulff, William D.

doi:10.1002/chem.201605955

Cited by 10 publications

(7 citation statements)

References 30 publications

(10 reference statements)

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“…Regardless of Bew’s reports, Wulff and coworkers had been contributing to the development of a multicomponent catalytic asymmetric aziridination reaction. The reported procedure starts with the addition of diazo ester compounds to N -protected aldimine catalyzed by a chiral Brønsted acid [55] (Scheme 15). This transformation usually affords cis -aziridine-2-carboxylate 59 in good yields and enantiomeric excess.…”

Section: Aziridinesmentioning

confidence: 99%

Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

et al. 2019

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Small ring heterocycles, such as epoxides and aziridines, are present in several natural products and are also highly versatile building blocks, frequently involved in the synthesis of numerous bioactive products and pharmaceuticals. Because of the potential for increased efficiency and selectivity, along with the advantages of environmentally benign synthetic procedures, multicomponent reactions (MCRs) have been explored in the synthesis and ring opening of these heterocyclic units. In this review, the recent advances in MCRs involving the synthesis and applications of epoxides and aziridines to the preparation of other heterocycles are discussed emphasizing the stereoselectivity of the reactions.

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Section: Aziridinesmentioning

confidence: 99%

Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

et al. 2019

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“…The proximity of the ions in the nonpolar solvent presumably allows VAPOL adduct 94 to control the facial selectivity of both the imine and diazoester. This method could provide highly diastereoselective and enantioselective aziridines, and has been applied in the synthesis of the precursors of florfenicol and β 3 -homo-amino acid [ 60 , 77 ].…”

Section: Vanol/vapolmentioning

confidence: 99%

Chiral Diol-Based Organocatalysts in Enantioselective Reactions

et al. 2018

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Organocatalysis has emerged as a powerful synthetic tool in organic chemistry in the last few decades. Among various classes of organocatalysis, chiral diol-based scaffolds, such as BINOLs, VANOLs, and tartaric acid derivatives, have been widely used to induce enantioselectivity due to the ability of the hydroxyls to coordinate with the Lewis acidic sites of reagents or substrates and create a chiral environment for the transformation. In this review, we will discuss the applications of these diol-based catalysts in different types of reactions, including the scopes of reactions and the modes of catalyst activation. In general, the axially chiral aryl diol BINOL and VANOL derivatives serve as the most competent catalyst for most examples, but examples of exclusive success using other scaffolds, herein, suggests that they should not be overlooked. Lastly, the examples, to date, are mainly from tartrate and biaryl diol catalysts, suggesting that innovation may be available from new diol scaffolds.

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“…BOROX catalysts derived from VAPOL ( 61 ), VANOL ( 62 ) and 7,7′‐di‐ tert ‐butylVANOL ( 100 , t Bu 2 VANOL) are highly efficient in dominating the stereochemical outcome of the multicomponent catalytic asymmetric aziridination reaction of aldehydes bearing chiral centers. Very high catalyst control has been observed with most of the aldehydes examined including aldehydes with chiral centers at α‐ or β‐positions or even chiral heterocyclic aldehydes . BOROX catalysts derived from VANOL or VAPOL ligands are similarly effective.…”

Section: Darzens Reaction and Related Processesmentioning

confidence: 99%

Catalytic Asymmetric Darzens and Aza‐Darzens Reactions for the Synthesis of Chiral Epoxides and Aziridines

et al. 2018

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This review presents an overview on the recent advances in the catalytic enantioselective Darzens and aza‐Darzens reactions for the synthesis of enantiopure three‐membered oxygen and nitrogen containing heterocycles. Since the synthesis of epoxides is the most widely explored, compared to their nitrogen counterparts, particularly true when asymmetric synthesis are considered, in the last decades several methodologies have appeared or improved and are now available for the preparation of aziridines in a highly stereo‐ and enantioselective manner. Catalytic asymmetric Darzens and aza‐Darzens reaction constitute an important tool in modern organic chemistry, as there is an increased interest in bioactive natural products and pharmaceutical agents that contain these skeletons.

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Catalyst‐Controlled Multicomponent Aziridination of Chiral Aldehydes

Cited by 10 publications

References 30 publications

Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines

Chiral Diol-Based Organocatalysts in Enantioselective Reactions

Catalytic Asymmetric Darzens and Aza‐Darzens Reactions for the Synthesis of Chiral Epoxides and Aziridines

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