Dirhodium(II) Tetrakis[N‐tetrachlorophthaloyl‐(S)‐tert‐leucinate]: A New Chiral Rh(II) Catalyst for Enantioselective Amidation of C—H Bonds.

Abstract

Enantioselective syntheses Enantioselective syntheses O 0031 Dirhodium(II) Tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate]: A New Chiral Rh(II) Catalyst for Enantioselective Amidation of C-H Bonds. -The amidation of benzylic C-H bonds with the phenyliodiane (II) is investigated in the presence of the title compound as catalyst. The observed enantioselectivities are the highest reported to date for Rh-catalyzed C-H amidation. -(YAMAWAKI, M.; TSUTSUI, H.; KITAGAKI, S.; ANADA, M.; HASHIMOTO*, S.; Tetrahedron Lett. 43 (2002) 52, 9561-9564; Grad. Sch. Pharm. Sci., Hokkaido Univ., Sapporo 060, Japan; Eng.) -Mais 12-035

Rh2(S‐1,2‐NTTL)4: A Novel Rh2(S‐PTTL)4 Analog With Lower Ligand Symmetry for Asymmetric Synthesis of Chiral Cyclopropylphosphonates

“…1), 25,32,33 with the tert-leucine derived catalyst Rh 2 (S-PTTL) 4 giving the highest asymmetric induction. [34][35][36][37][38][39][40] This has been further developed by the same group and others to include many other analogs. 25,[41][42][43][44] Müller et al used the same scaffold and emerged with Rh 2 (S-NTTL) 4 as a catalyst derived from N-1,8-naphthaloyl-(S)-tert-leucine.…”

A New Ligand Design Based on London Dispersion Empowers Chiral Bismuth–Rhodium Paddlewheel Catalysts

“…Initial attempts to remedy this issue by tailoring the phthalimido groups largely met with failure. Although perhalogenated phthalimides have proven advantageous in many cases, 47 − 50 the heterobimetallic complex 2b gave almost racemic product. The X-ray structure revealed the likely cause: 2b features an inverted calyx, in which the “chiral” environment envelopes the unreactive Bi(+2) site, whereas the Rh-atom sees the tert -butyl substituents.…”

Chiral Dirhodium(II) Carboxylates: New Insights into the Effect of Ligand Stereo-Purity on Catalyst Structure and Enantioselectivity

“…Out of the large dirhodium(II) catalyst family and by following different approaches for catalyst design, several highly enantioselective dirhodium(II) carboxylate catalysts have been reported to date [13,[35][36][37][38][39][40][41][42][43][44]. Our research group, for example, has recently reported a novel approach for the design of dirhodium(II) tetracarboxylate complexes derived from S-amino acid ligands [35,36,45].…”