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Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary α,α-heterodiaryl carboxylic esters.
Org Lett. 2011 Oct 07; 13(19):5370-3.OL

Abstract

A rhodium-catalyzed one-pot three-component coupling reaction was developed for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. This reaction involves cross-coupling of the arylrhodium(I) complexes with α-aryldiazoacetates to form oxa-π-allylrhodium complexes. With KOtBu and alkyl halides, tandem alkylation of the allyl complex occurs to form a quaternary stereocenter at the carbenic carbon.

Authors+Show Affiliations

State Key Laboratory for Chirosciences, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21894953

Citation

Tsoi, Yuk-Tai, et al. "Rhodium-catalyzed Cross-coupling Reaction of Arylboronates and Diazoesters and Tandem Alkylation Reaction for the Synthesis of Quaternary Α,α-heterodiaryl Carboxylic Esters." Organic Letters, vol. 13, no. 19, 2011, pp. 5370-3.
Tsoi YT, Zhou Z, Yu WY. Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. Org Lett. 2011;13(19):5370-3.
Tsoi, Y. T., Zhou, Z., & Yu, W. Y. (2011). Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. Organic Letters, 13(19), 5370-3. https://doi.org/10.1021/ol2022577
Tsoi YT, Zhou Z, Yu WY. Rhodium-catalyzed Cross-coupling Reaction of Arylboronates and Diazoesters and Tandem Alkylation Reaction for the Synthesis of Quaternary Α,α-heterodiaryl Carboxylic Esters. Org Lett. 2011 Oct 7;13(19):5370-3. PubMed PMID: 21894953.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed cross-coupling reaction of arylboronates and diazoesters and tandem alkylation reaction for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. AU - Tsoi,Yuk-Tai, AU - Zhou,Zhongyuan, AU - Yu,Wing-Yiu, Y1 - 2011/09/06/ PY - 2011/9/8/entrez PY - 2011/9/8/pubmed PY - 2012/1/18/medline SP - 5370 EP - 3 JF - Organic letters JO - Org Lett VL - 13 IS - 19 N2 - A rhodium-catalyzed one-pot three-component coupling reaction was developed for the synthesis of quaternary α,α-heterodiaryl carboxylic esters. This reaction involves cross-coupling of the arylrhodium(I) complexes with α-aryldiazoacetates to form oxa-π-allylrhodium complexes. With KOtBu and alkyl halides, tandem alkylation of the allyl complex occurs to form a quaternary stereocenter at the carbenic carbon. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21894953/Rhodium_catalyzed_cross_coupling_reaction_of_arylboronates_and_diazoesters_and_tandem_alkylation_reaction_for_the_synthesis_of_quaternary_αα_heterodiaryl_carboxylic_esters_ L2 - https://doi.org/10.1021/ol2022577 DB - PRIME DP - Unbound Medicine ER -