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Enantioselective synthesis of trans-aryl- and -heteroaryl-substituted cyclopropylboronates by copper(I)-catalyzed reactions of allylic phosphates with a diboron derivative.
J Am Chem Soc. 2010 Aug 25; 132(33):11440-2.JA

Abstract

A new asymmetric route for the synthesis of trans-2-aryl- and -heteroaryl-substituted cyclopropylboronates has been developed. (Z)-3-arylallylic phosphates were converted to the optically active products with high yield and diastereo- and enantioselectivity through a copper(I)-catalyzed reaction with a diboron derivative. Under mild reaction conditions, the reaction affords the arylcyclopropane products with a functional group and a heteroaromatic group in a highly enantioselective manner. When (E)-allylic phosphates were used as substrates, a ligand-controlled product switch between the trans and cis configurations was observed.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Zhong C
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan.
Kunii S
No affiliation info available
Kosaka Y
No affiliation info available
Sawamura M
No affiliation info available
Ito H
No affiliation info available

MeSH

Allyl CompoundsBoron CompoundsCatalysisCopperCyclopropanesMolecular StructureOrganophosphatesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

20684557

Citation

Zhong, Chongmin, et al. "Enantioselective Synthesis of Trans-aryl- and -heteroaryl-substituted Cyclopropylboronates By copper(I)-catalyzed Reactions of Allylic Phosphates With a Diboron Derivative." Journal of the American Chemical Society, vol. 132, no. 33, 2010, pp. 11440-2.
Zhong C, Kunii S, Kosaka Y, et al. Enantioselective synthesis of trans-aryl- and -heteroaryl-substituted cyclopropylboronates by copper(I)-catalyzed reactions of allylic phosphates with a diboron derivative. J Am Chem Soc. 2010;132(33):11440-2.
Zhong, C., Kunii, S., Kosaka, Y., Sawamura, M., & Ito, H. (2010). Enantioselective synthesis of trans-aryl- and -heteroaryl-substituted cyclopropylboronates by copper(I)-catalyzed reactions of allylic phosphates with a diboron derivative. Journal of the American Chemical Society, 132(33), 11440-2. https://doi.org/10.1021/ja103783p
Zhong C, et al. Enantioselective Synthesis of Trans-aryl- and -heteroaryl-substituted Cyclopropylboronates By copper(I)-catalyzed Reactions of Allylic Phosphates With a Diboron Derivative. J Am Chem Soc. 2010 Aug 25;132(33):11440-2. PubMed PMID: 20684557.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective synthesis of trans-aryl- and -heteroaryl-substituted cyclopropylboronates by copper(I)-catalyzed reactions of allylic phosphates with a diboron derivative. AU - Zhong,Chongmin, AU - Kunii,Shun, AU - Kosaka,Yuki, AU - Sawamura,Masaya, AU - Ito,Hajime, PY - 2010/8/6/entrez PY - 2010/8/6/pubmed PY - 2010/12/14/medline SP - 11440 EP - 2 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 132 IS - 33 N2 - A new asymmetric route for the synthesis of trans-2-aryl- and -heteroaryl-substituted cyclopropylboronates has been developed. (Z)-3-arylallylic phosphates were converted to the optically active products with high yield and diastereo- and enantioselectivity through a copper(I)-catalyzed reaction with a diboron derivative. Under mild reaction conditions, the reaction affords the arylcyclopropane products with a functional group and a heteroaromatic group in a highly enantioselective manner. When (E)-allylic phosphates were used as substrates, a ligand-controlled product switch between the trans and cis configurations was observed. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/20684557/Enantioselective_synthesis_of_trans_aryl__and__heteroaryl_substituted_cyclopropylboronates_by_copper_I__catalyzed_reactions_of_allylic_phosphates_with_a_diboron_derivative_ L2 - https://doi.org/10.1021/ja103783p DB - PRIME DP - Unbound Medicine ER -