Phosphine-Catalyzed Crossed Rauhut–Currier-Type Coupling and [3 + 2]-Cycloaddition of 2-Alkylidene-3-oxindoles with Alkenes and Allenes to Access β,γ-Unsaturated Enones and Polycyclic Oxindoles DOI
Saikumar Banda, Lasse Johannßen,

Alice Voss

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13263 - 13271

Published: Sept. 6, 2024

Dihydroazepino[1,2-

Language: Английский

Enantioselective synthesis of molecules with multiple stereogenic elements DOI Creative Commons
Arthur Gaucherand, Expédite Yen‐Pon,

Antoine Domain

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(22), P. 11165 - 11206

Published: Jan. 1, 2024

This review explores the fascinating world of molecules featuring multiple stereogenic elements, unraveling different strategies designed over years for their enantioselective synthesis.

Language: Английский

Citations

13
Synthesis of Chiral Endocyclic Allenes and Alkynes via Pd-Catalyzed Asymmetric Higher-Order Dipolar Cycloaddition DOI

Bin Shi,

Meng Xiao,

Jin-Pu Zhao

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 18, 2024

A Pd-catalyzed asymmetric higher-order dipolar cycloaddition between allenyl carbonates and azadienes is achieved by exploiting novel alkylidene-π-allyl-Pd dipoles. This research provides a modular platform for the synthesis of challenging chiral endocyclic allenes bearing medium-sized heterocyclic motif centrally stereocenter in good yields with high enantio- diastereoselectivities (29 examples, up to 97% yield, 97:3 er >19:1 dr). Experimental computational studies elucidate possible reaction mechanism observed stereochemical results. Based on mechanistic understanding, new π-propargyl-Pd dipole was designed further extend success higher order strategy 10-membered alkynes from propargyl (13 98% yield 94.5:5.5 er).

Language: Английский

Citations

8
Transition-metal-free regioselective synthesis of spiro-oxazolidines through [3 + 2] annulation reactions of azadienes with haloalcohols DOI Creative Commons

Amol T. Savekar,

Sonali M. Vitnor,

Vishal B. Karande

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(14), P. 10634 - 10638

Published: Jan. 1, 2025

The transition-metal-free regioselective [3 + 2] annulation of azadienes with haloalcohols for the preparation highly functionalized spiro-oxazolidines is experimentally simple, broad substrate scope, good yields, and excellent regioselectivity.

Language: Английский

Citations

0
Phosphine-Catalyzed Crossed Rauhut–Currier-Type Coupling and [3 + 2]-Cycloaddition of 2-Alkylidene-3-oxindoles with Alkenes and Allenes to Access β,γ-Unsaturated Enones and Polycyclic Oxindoles DOI
Saikumar Banda, Lasse Johannßen,

Alice Voss

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13263 - 13271

Published: Sept. 6, 2024

Dihydroazepino[1,2-

Language: Английский

Citations

0