Retracted article: Enantioselectivity of aza-MBH-type reaction of nitroalkene to N-tosylimine catalyzed by thiourea-tertiary amine: a theoretical study

Lu, Nan; Lin, Meng; Chen, Dezhan; Zhang, Guiqiu

doi:10.1039/c1ra00015b

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Stereoselectivity Of Mbh/aza-mbh Reaction1

Recent Mechanistic Insights Into the Mbh/aza-mbh Reaction An...1

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Cited by 7 publications

(2 citation statements)

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“…In 2011, Chen and co-workers investigated the detailed mechanism for the thiourea-tertiary amine-catalyzed enantioselective aza-MBH reaction of nitroalkene and N-tosylimine by DFT calculations. 29 They proposed the mechanism as shown in Scheme 12. The Lewis base catalyst 33 activates the nitroalkene 34 by the tertiary amine moiety via a weak covalent bond, generating the zwitterionic intermediate Int0.…”

Section: Stereoselectivity Of Mbh/aza-mbh Reactionmentioning

confidence: 99%

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Recent Advances in Organocatalytic Asymmetric Morita–Baylis–Hillman/aza-Morita–Baylis–Hillman Reactions

2013

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Section: Stereoselectivity Of Mbh/aza-mbh Reactionmentioning

confidence: 99%

Section: Recent Mechanistic Insights Into the Mbh/aza-mbh Reaction An...mentioning

confidence: 99%

Recent Advances in Organocatalytic Asymmetric Morita–Baylis–Hillman/aza-Morita–Baylis–Hillman Reactions

2013

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Morita–Baylis–Hillman Reactions with Nitroalkenes: A Case Study

2015

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We report on the use of a highly reactive super‐DMAP catalyst in Morita–Baylis–Hillman (MBH) reactions of nitroalkenes with ethyl glyoxylate, which result in excellent conversions and short reaction times with, importantly, very low catalyst loading. An extensive study of this particular reaction is presented, which examines all mechanistic and experimental details. Several critical points were hence uncovered that include the correlation between reaction efficiency and Lewis basicity of the catalyst; the double role played by the promoter, primarily as a nucleophilic activator towards the nitroalkene, and as a Brønsted base that triggers glyoxylate depolymerisation. More generally, the limitations in the choice of electrophiles that can engage efficiently in MBH‐type transformations are rationalized by the competition between a productive pathway and a nitroalkene polymerization process. Other aspects of this transformation, used as a case study, are presented in the light of physical organic chemistry.

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The mechanism of the NHC catalyzed aza-Morita–Baylis–Hillman reaction: insights into a new substrate-catalyzed bimolecular pathway

Verma

Sunoj

2014

Org. Biomol. Chem.

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Retracted article: Enantioselectivity of aza-MBH-type reaction of nitroalkene to N-tosylimine catalyzed by thiourea-tertiary amine: a theoretical study

Cited by 7 publications

References 39 publications

Recent Advances in Organocatalytic Asymmetric Morita–Baylis–Hillman/aza-Morita–Baylis–Hillman Reactions

Recent Advances in Organocatalytic Asymmetric Morita–Baylis–Hillman/aza-Morita–Baylis–Hillman Reactions

Morita–Baylis–Hillman Reactions with Nitroalkenes: A Case Study

The mechanism of the NHC catalyzed aza-Morita–Baylis–Hillman reaction: insights into a new substrate-catalyzed bimolecular pathway

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