1,2- and 1,4-cycloaddition of chlorosulfonyl isocyanate to dienes

Moriconi, Emil J.; Meyer, W. C.

doi:10.1016/s0040-4039(01)99111-7

Cited by 23 publications

(6 citation statements)

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“…Following deprotection of the β-lactam nitrogen with cerric ammonium nitrate, the cis - and trans -β-lactam intermediates were separated from one another and independently acylated with the desired acid chloride, illustrated in Scheme for 2a . Any of the required acyl groups that were not commercially available were prepared by well-established methods .…”

Section: Chemistrymentioning

confidence: 99%

Identification and Initial Structure−Activity Relationships of a Novel Class of Nonpeptide Inhibitors of Blood Coagulation Factor Xa

et al. 1998

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The discovery and some of the basic structure-activity relationships of a series of novel nonpeptide inhibitors of blood coagulation Factor Xa is described. These inhibitors are functionalized beta-alanines, exemplified by 2a. Docking experiments placing 2a in the active site of Factor Xa implied that the most expeditious route to enhancing in vitro potency was to modify the group occupying the S3 site of the enzyme. Increasing the hydrophobic contacts between the inhibitor and the enzyme in this region led to 8, which has served as the prototype for this series. In addition, an enantioselective synthesis of these substituted beta-alanines was also developed.

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Section: Chemistrymentioning

confidence: 99%

Identification and Initial Structure−Activity Relationships of a Novel Class of Nonpeptide Inhibitors of Blood Coagulation Factor Xa

et al. 1998

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“…Taken together, these reactions should facilitate the construction of fused heterocycles. Keywords: lactams · cyclobutanes · domino reactions · electrocyclic reactions · pericyclic reactions cycloaddition between a diene, such as isoprene, and chlorosulfonyl isocyanate [10] to afford the N-chlorosulfonyl blactam, which is cleanly reduced to the corresponding N-H b-lactam with aqueous sodium sulfite. [11] The N-H b-lactam is then cross coupled with a vinyl iodide [12] under copper-catalysed coupling conditions [13] to yield the corresponding Nvinyl b-lactam.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Highly Substituted Cyclobutane Fused‐Ring Systems from N‐Vinyl β‐Lactams through a One‐Pot Domino Process

Cheung

Yudin

2010

Chemistry A European J

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In this contribution, aminocyclobutanes, as well as eight-membered enamide rings, have been made from N-vinyl beta-lactams. The eight-membered products have been formed by a [3,3]-sigmatropic rearrangement, whereas the aminocyclobutanes have been derived from a domino [3,3]-rearrangement/6pi-electrocyclisation process. The aminocyclobutanes have been obtained in a highly diastereoselective fashion. The cyclobutane ring system tolerates fusion even if adjacent quaternary centres are present. Systems containing up to four fused rings are readily accessible. The reaction profile has been investigated by using Gaussian 03. This study suggests that two reaction pathways for aminocyclobutane formation are possible. In one pathway the [3,3]-sigmatropic rearrangement is the rate-limiting step and in the second pathway the electrocyclisation is rate limiting. Taken together, these reactions should facilitate the construction of fused heterocycles.

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“…The β-lactam starting materials can be prepared on a multigram scale in three steps that include a single purification (Scheme ). The synthesis begins with a cycloaddition between isoprene and chlorosulfonyl isocyanate to afford the N -chlorosulfonyl β-lactam that is cleanly reduced to the corresponding N -H β-lactam with aqueous sodium sulfite . The β-lactam is then cross coupled with an appropriate vinyl iodide under copper catalysis to give the corresponding N -vinyl-β-lactam.…”

mentioning

confidence: 99%