Enantiopure 2-Aryl-2-Methyl Cyclopentanones by an Asymmetric Chelation-Controlled Heck Reaction Using Aryl Bromides: Increased Preparative Scope and Effect of Ring Size on Reactivity and Selectivity

Enantiopure 2-Aryl-2-Methyl Cyclopentanones by an Asymmetric Chelation-Controlled Heck Reaction Using Aryl Bromides : Increased Preparative Scope and Effect of Ring Size on Reactivity and Selectivity

Datta, Gopal K. (author): Uppsala universitet,Avdelningen för organisk farmaceutisk kemi

Nordeman, Patrik (author): Uppsala universitet,Avdelningen för organisk farmaceutisk kemi

Dackenberg, Jakob (author): Uppsala universitet,Avdelningen för organisk farmaceutisk kemi

Nilsson, Peter (author): Uppsala universitet,Institutionen för läkemedelskemi,ORGFARM

Hallberg, Anders (author): Uppsala universitet,Avdelningen för organisk farmaceutisk kemi

Larhed, Mats (author): Uppsala universitet,Avdelningen för organisk farmaceutisk kemi

(creator_code:org_t)

Elsevier BV, 2008
2008
English.
In: Tetrahedron. - : Elsevier BV. - 0957-4166 .- 1362-511X. ; 19:9, s. 1120-1126

Related links:: https://urn.kb.se/re...; show more...; https://doi.org/10.1...; show less...

Abstract Subject headings

Quaternary 2-aryl-2-methyl cyclopentanones were obtained in 85–94% ee via Pd(0)-catalyzed chelation-controlled asymmetric arylation of a cyclopentenyl ether with aryl bromides and subsequent hydrolysis. Two new cyclohexenyl ethers were synthesized and evaluated as Heck substrates with both aryl iodides and bromides under different reaction conditions. Arylations of the six-membered vinyl ether 1-methyl-2-(S)-(cyclohex-1-enyloxymethyl)-pyrrolidine with aryl bromides were achieved with t-Bu3P-promoted palladium catalysis using either classical or microwave heating. Isolated Heck products were also obtained in high diastereoselectivities (94–98% de).

By the author/editor: Datta, Gopal K.; Nordeman, Patrik; Dackenberg, Jako ...; Nilsson, Peter; Hallberg, Anders; Larhed, Mats

About the subject

MEDICAL AND HEALTH SCIENCES: MEDICAL AND HEAL ...; and Basic Medicine; and Pharmaceutical S ...

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