Journal of the American Chemical Society. 2011 Oct 26;133(42):16794-7. doi: 10.1021/ja2077813 Q115.62025

Ate complexes of secondary boronic esters as chiral organometallic-type nucleophiles for asymmetric synthesis

手性杂环硼酯亚胺金属配合物作为不对称合成的手性亲核试剂翻译改进

Robin Larouche-Gauthier¹, Tim G Elford, Varinder K Aggarwal

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¹ School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, United Kingdom.

DOI: 10.1021/ja2077813 PMID: 21939203

The addition of an aryllithium reagent to a secondary boronic ester leads to an intermediate boron-ate complex that behaves as a chiral nucleophile, reacting with a broad range of electrophiles with inversion of stereochemistry. Depending on the electrophile, the C-B bond can be converted into C-I, C-Br, C-Cl, C-N, C-O, and C-C, all with very high levels of stereocontrol. This discovery now adds a new, readily available, configurationally stable, chiral organometallic-type reagent to the arsenal of methods for use in asymmetric organic synthesis.

Keywords：secondary boronic esters; asymmetric synthesis

关键词：secondary 酯; 不对称合成

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期刊名：Journal of the american chemical society

缩写：J AM CHEM SOC

ISSN：0002-7863

e-ISSN：1520-5126

IF/分区：15.6/Q1

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Ate complexes of secondary boronic esters as chiral organometallic-type nucleophiles for asymmetric synthesis

手性杂环硼酯亚胺金属配合物作为不对称合成的手性亲核试剂翻译改进

Rh-catalyzed enantioselective hydrogenation of vinyl boronates for the construction of secondary boronic esters

铑催化烯烃硼酸酯的不对称氢化反应合成二级光学纯硼酸酯化合物

Stereospecific couplings of secondary and tertiary boronic esters

二级和三级硼酸酯的立体专一性偶联反应

Asymmetric Synthesis of Substituted anti-β-Fluorophenylalanines

取代反式-β-氟苯丙氨酸的不对称合成

Asymmetric Synthesis of P-Stereogenic Phosphinic Amides via Pd(0)-Catalyzed Enantioselective Intramolecular C-H Arylation

手性磷酸胺的不对称合成：钯催化内消旋C-H芳构化反应

Asymmetric synthesis of polyfunctionalized pyrrolidines from sulfinimine-derived pyrrolidine 2-phosphonates. Synthesis of pyrrolidine 225C

手性磷鎓硫亚胺𬭩盐的制备及多功能化吡咯烷的不对称合成研究：化合物225C的合成

Functionalized chiral vinyl aminosulfoxonium salts: asymmetric synthesis and application to the synthesis of enantiopure unsaturated prolines, beta,gamma-dehydro amino acids, and cyclopentanoid keto aminosulfoxonium ylides

功能化的手性乙烯亚胺氨基锍盐：不对称合成及其在非对映异构体纯烯丙基脯氨酸、β，γ-脱氢氨基酸及环戊基酮氨基锍盐亚胺离子的合成中的应用

Dehydrogenases and transaminases in asymmetric synthesis

不对称合成中的脱氢酶和转氨酶

Asymmetric synthesis of the fully functionalized six-membered A-ring of siphonol A

西波诺尔A完全官能化的六元A环的不对称合成

Ate complexes of secondary boronic esters as chiral organometallic-type nucleophiles for asymmetric synthesis

手性杂环硼酯亚胺金属配合物作为不对称合成的手性亲核试剂 翻译改进

Rh-catalyzed enantioselective hydrogenation of vinyl boronates for the construction of secondary boronic esters

铑催化烯烃硼酸酯的不对称氢化反应合成二级光学纯硼酸酯化合物

Stereospecific couplings of secondary and tertiary boronic esters

二级和三级硼酸酯的立体专一性偶联反应

Asymmetric Synthesis of Substituted anti-β-Fluorophenylalanines

取代反式-β-氟苯丙氨酸的不对称合成

Asymmetric Synthesis of P-Stereogenic Phosphinic Amides via Pd(0)-Catalyzed Enantioselective Intramolecular C-H Arylation

手性磷酸胺的不对称合成：钯催化内消旋C-H芳构化反应

Asymmetric synthesis of polyfunctionalized pyrrolidines from sulfinimine-derived pyrrolidine 2-phosphonates. Synthesis of pyrrolidine 225C

手性磷鎓硫亚胺𬭩盐的制备及多功能化吡咯烷的不对称合成研究：化合物225C的合成

Functionalized chiral vinyl aminosulfoxonium salts: asymmetric synthesis and application to the synthesis of enantiopure unsaturated prolines, beta,gamma-dehydro amino acids, and cyclopentanoid keto aminosulfoxonium ylides

功能化的手性乙烯亚胺氨基锍盐：不对称合成及其在非对映异构体纯烯丙基脯氨酸、β，γ-脱氢氨基酸及环戊基酮氨基锍盐亚胺离子的合成中的应用

Dehydrogenases and transaminases in asymmetric synthesis

不对称合成中的脱氢酶和转氨酶

Asymmetric synthesis of the fully functionalized six-membered A-ring of siphonol A

西波诺尔A完全官能化的六元A环的不对称合成

手性杂环硼酯亚胺金属配合物作为不对称合成的手性亲核试剂翻译改进