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Copper-Catalyzed Enantioselective Substitution of Allylic Carbonates with Diboron: An Efficient Route to Optically Active α-Chiral Allylboronates
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Abstract
A method for the synthesis of α-chiral allylboronates featuring the Cu(I)-catalyzed enantioselective substitution of readily available allylic carbonates with a diboron is described. Using this method, various α-chiral allylboronates, including functionalized allylboronates, were successfully synthesized, with high enantiomeric purity.
Citing Articles
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This article has been cited by 33 ACS Journal articles (5 most recent appear below).
Copper(I)-Catalyzed Boryl Substitution of Unactivated Alkyl Halides
Hajime Ito and Koji KubotaOrganic Letters2012 14 (3), 890-893Copper(I)-Catalyzed Boryl Substitution of Unactivated Alkyl Halides
Hajime Ito and Koji KubotaOrganic Letters2012 14 (3), 890-893Borylation of alkyl halides with diboron proceeded in the presence of a copper(I)/Xantphos catalyst and a stoichiometric amount of K(O-t-Bu) base. The boryl substitution proceeded with normal and secondary alkyl chlorides, bromides, and iodides, but alkyl ...
Stereoconvergent Synthesis of Chiral Allylboronates from an E/Z Mixture of Allylic Aryl Ethers Using a 6-NHC−Cu(I) Catalyst
Jin Kyoon Park, Hershel H. Lackey, Brian A. Ondrusek, and D. Tyler McQuadeJournal of the American Chemical Society2011 133 (8), 2410-2413Stereoconvergent Synthesis of Chiral Allylboronates from an E/Z Mixture of Allylic Aryl Ethers Using a 6-NHC−Cu(I) Catalyst
Jin Kyoon Park, Hershel H. Lackey, Brian A. Ondrusek, and D. Tyler McQuadeJournal of the American Chemical Society2011 133 (8), 2410-2413We present a 6-NHC−Cu(I) complex that provides α-substituted allylboronates using allylic aryl ether substrates. The method was discovered by comparison of the chemoselectivities exhibited by complexes 1a, 1b, 2, and 3. We observed that 1a preferentially ...
Copper(I)−Secondary Diamine Complex-Catalyzed Enantioselective Conjugate Boration of Linear β,β-Disubstituted Enones
I-Hon Chen, Motomu Kanai, and Masakatsu ShibasakiOrganic Letters2010 12 (18), 4098-4101Copper(I)−Secondary Diamine Complex-Catalyzed Enantioselective Conjugate Boration of Linear β,β-Disubstituted Enones
I-Hon Chen, Motomu Kanai, and Masakatsu ShibasakiOrganic Letters2010 12 (18), 4098-4101A copper(I)−chiral secondary diamine (L-e) complex catalyzes an enantioselective conjugate boration of β,β-disubstituted enones in high yields and up to 99% ee. Product chiral tertiary organoboronates can be converted to enantiomerically enriched cross-...
Enantioselective Synthesis of trans-Aryl- and -Heteroaryl-Substituted Cyclopropylboronates by Copper(I)-Catalyzed Reactions of Allylic Phosphates with a Diboron Derivative
Chongmin Zhong, Shun Kunii, Yuki Kosaka, Masaya Sawamura and Hajime ItoJournal of the American Chemical Society2010 132 (33), 11440-11442Enantioselective Synthesis of trans-Aryl- and -Heteroaryl-Substituted Cyclopropylboronates by Copper(I)-Catalyzed Reactions of Allylic Phosphates with a Diboron Derivative
Chongmin Zhong, Shun Kunii, Yuki Kosaka, Masaya Sawamura and Hajime ItoJournal of the American Chemical Society2010 132 (33), 11440-11442A 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 ...
Palladium-Catalyzed Synthesis of Enantiomerically Pure α-Substituted Allylboronic Esters and Their Addition to Aldehydes
Enrique Fernández, Jörg Pietruszka and Wolfgang FreyThe Journal of Organic Chemistry2010 75 (16), 5580-5589Palladium-Catalyzed Synthesis of Enantiomerically Pure α-Substituted Allylboronic Esters and Their Addition to Aldehydes
Enrique Fernández, Jörg Pietruszka and Wolfgang FreyThe Journal of Organic Chemistry2010 75 (16), 5580-5589Tartrate-derived boronic esters 2 can be subjected to palladium-catalyzed carbonyl allylations with SnCl2 to obtain enantiomerically pure α-substituted allylboronic esters 8 and 9. The reaction proceeds regioselectively and with high, simple ...
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History
- Published In Issue December 05, 2007
- Received September 3, 2007
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