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Rhodium(II) Catalyzed Synthesis of Macrocycles Incorporating Oxindole via O-H/N-H Insertion Reactions

Rhodium(II) Catalyzed Synthesis of Macrocycles Incorporating Oxindole via O-H/N-H Insertion Reactions

Sengodagounder Muthusamy, Thangaraju Karikalan

Org Biomol Chem. 2014 Dec 7;12(45):9243-56.

PMID: 25302664

Abstract:

A wide variety of 10- to 29-membered oxaza-macrocycles incorporating an oxindole unit were synthesized in good yield via rhodium(II) acetate dimer catalyzed intramolecular O-H/N-H insertion reactions. Interestingly, synthesis of C2-symmetric macrocycles in moderate yield was also demonstrated via head to tail dimerization involving double intermolecular O-H insertion when the spacer length was decreased. The synthesis of chiral macrocycles was also delineated. This study reveals the effect of spacer length on inter- or intramolecular insertion reactions with the remotely placed hydroxyl/amino group.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP15956282	Rhodium(II) acetate dimer		15956-28-2	Price

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