Camphor‐Derived N‐Acryloyl and N‐Crotonoyl Sultams: Practical Activated Dienophiles in Asymmetric Diels‐alder Reactions. Preliminary Communication

doi:10.1002/HLCA.19840670527

Paper

Camphor‐Derived N‐Acryloyl and N‐Crotonoyl Sultams: Practical Activated Dienophiles in Asymmetric Diels‐alder Reactions. Preliminary Communication

Published Aug 8, 1984 · W. Oppolzer, C. Chapuis, G. Bernardinelli

Helvetica Chimica Acta

Q2 SJR score

195

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Starting from (+)-camphor-10-sulfonyl chloride (5), the crystalline sultam 8 was easily prepared. Lewis-acid-promoted Diels-Alder additions of the crystalline N-acry-loyl and N-crotonoyl derivatives 9 and 10, respectively, to cyclopentadiene and 1,3-butadiene at −130 to −78° furnished adducts 11, 12 and 17 with high chiral efficiency. Crystallization of the adducts and nondestructive removal of 8 gave either alcohols 13, 14 and 18 ir acid 19 in 99% enantiomeric purity. The sense of induction was reversed on using the enantiomer of 8 as the auxiliary. The structure of 10 was established by X-ray diffraction analysis.

Highly Cited

Study Snapshot

Camphor-derived N-acryloyl and N-crotonoyl sultams can be used as effective activated dienophiles in asymmetric Diels-Alder reactions, yielding high chiral efficiency and enantiomeric purity.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Camphor‐Derived N‐Acryloyl and N‐Crotonoyl Sultams: Practical Activated Dienophiles in Asymmetric Diels‐alder Reactions. Preliminary Communication

Sign up to use Study Snapshot

References

Citations

Synthetic pathways to create asymmetric center at C1 position of 1-substituted-tetrahydro-β-carbolines – a review

Chiral 1-substituted-THCs show potential for MAO inhibitory activity, benzodiazepine receptor binding, and antimalarial effectiveness against chloroquine-resistant Plasmodium falciparum, with various synthetic approaches available for their introduction.

Discovery of Carboxylesterases via Metagenomics: Putative Enzymes that Contribute to Chemical Kinetic Resolution

Recent discoveries of carboxylesterases via genome mining show potential in chemical kinetic resolution of compounds with pharmaceutical and biotechnological applications.

Kinetic Resolution of Nearly Symmetric 3-Cyclohexene-1-carboxylate Esters Using a Bacterial Carboxylesterase Identified by Genome Mining.

CarEst3 efficiently hydrolyzes racemic methyl 3-cyclohexene-1-carboxylate with a nearly symmetric structure, yielding (S)-CHCM with a >99% enantioselectiveness and high substrate tolerance.

Twisting and turning the sulfonamide bond: synthetic, quantum chemical and crystallographic study.

Paquette's sultams, bridged bicyclic sultams with bridgehead nitrogen atom, were synthesized and studied, with the s-character of the nitrogen lone pair being the most important factor defining properties of the S-N bond.

Asymmetric Synthesis of an Advanced Tetracyclic Framework of (+)-Sarain A.

This study developed an asymmetric synthetic approach to create an advanced tetracyclic framework of (+)-sarain A, a marine-derived alkaloid with potential therapeutic applications.

Stereoselective α-Hydroxylation of Amides Using Oppolzer's Sultam as Chiral Auxiliary.

This study developed a highly stereoselective -hydroxylation of amides using Oppolzer's sultam, resulting in good yield and excellent diastereoselectivity, with recyclability of the chiral auxiliary.