Rhodium-Catalyzed Regio- and Enantioselective Allylic Sulfonylation from Sulfonyl Hydrazides

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3693 - 3697

Published: May 15, 2023

A highly regio- and enantioselective allylic sulfonylation has been developed with rhodium bisoxazolinephosphine (NPN*) ligands from racemic branched carbonates readily available sulfonyl hydrazides under neutral conditions. Branch-selective sulfones a >20:1 branch:linear ratio >99% ee could be synthesized in ≤96% yield. Both Z E linear also converted into the same chiral high enantioselectivities.

Language: Английский

---

Organocatalytic Asymmetric Morita–Baylis–Hillman Reaction of Isatins with Vinyl Sulfones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3802 - 3807

Published: Feb. 23, 2023

The organocatalytic asymmetric Morita-Baylis-Hillman (MBH) reaction of isatin derivatives with various vinyl sulfones is disclosed. Chiral sulfone-containing 3-hydroxyoxindoles were produced in good to high yields and ee's. This report displays an unprecedented example apply activated alkenes sulfone moiety other than carbonyl groups MBH reactions provides efficient strategy incorporate the functional group for synthesis chiral 3-hydroxyoxindoles.

Language: Английский

---

Enantioselective Ir-Catalyzed Hydrogenation of Terminal Homoallyl Sulfones: Total Synthesis of (−)-Curcumene

Organic Letters, Journal Year: 2023, Volume and Issue: 25(9), P. 1453 - 1457

Published: March 1, 2023

A novel methodology for the preparation of chiral methyl benzylic compounds is reported. Terminal homoallyl sulfones were prepared from alcohols, which are easily accessible through recently reported Lewis acid isomerization oxetanes. The iridium-catalyzed asymmetric hydrogenation homoallylic afforded γ-chiral with excellent enantioselectivities (up to 98% ee). synthetic potential this was demonstrated by total synthesis (R)-(−)-curcumene.

Language: Английский

---

Catalytic Enantioselective Electrophilic Difunctionalization of Unsaturated Sulfones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4514 - 4519

Published: May 17, 2024

An efficient protocol of enantioselective thiolative azidation sulfone-tethered alkenes via a chiral chalcogenide catalyzed electrophilic reaction is disclosed. A series enantioenriched sulfones bearing remote stereogenic centers was achieved with good yields and high enantioselectivities linear unsaturated cyclic sulfones. Mechanistic studies revealed the importance sulfone group in improvement reactivity enantioselectivity reaction.

Language: Английский

---

Construction of enantioenriched small molecular scaffolds through biocatalytic dynamic kinetic resolution

Tetrahedron, Journal Year: 2024, Volume and Issue: 166, P. 134207 - 134207

Published: Aug. 22, 2024

Language: Английский

---