Rhodium-Catalyzed Enantioselective Addition of Arylboroxines to Isatin-Derived N-Boc Ketimines Using Chiral Phosphite–Olefin Ligands: Asymmetric Synthesis of 3-Aryl-3-amino-2-oxindoles

Yue-Na Yu; Wei-Yi Qi; Chun-Yan Wu; Ming-Hua Xu

doi:10.1021/acs.orglett.9b02787

Rhodium-Catalyzed Enantioselective Addition of Arylboroxines to Isatin-Derived N-Boc Ketimines Using Chiral Phosphite–Olefin Ligands: Asymmetric Synthesis of 3-Aryl-3-amino-2-oxindoles

Organic Letters ◽

10.1021/acs.orglett.9b02787 ◽

2019 ◽

Vol 21 (18) ◽

pp. 7493-7497 ◽

Cited By ~ 5

Author(s):

Yue-Na Yu ◽

Wei-Yi Qi ◽

Chun-Yan Wu ◽

Ming-Hua Xu

Keyword(s):

Asymmetric Synthesis ◽

Enantioselective Addition ◽

Chiral Phosphite

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Asymmetric synthesis of N-diphenylphosphinoylamines by solvent-free enantioselective addition of dialkylzincs to N-diphenylphosphinoylimines

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/b106775n ◽

2001 ◽

pp. 2912-2914 ◽

Cited By ~ 17

Author(s):

Itaru Sato ◽

Ryo Kodaka ◽

Kenso Soai

Keyword(s):

Asymmetric Synthesis ◽

Solvent Free ◽

Enantioselective Addition

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ChemInform Abstract: Rhodium-Catalyzed Highly Enantioselective Addition of Arylboronic Acids to Cyclic Aldimines: Practical Asymmetric Synthesis of Cyclic Sulfamidates.

ChemInform ◽

10.1002/chin.201352195 ◽

2013 ◽

Vol 44 (52) ◽

pp. no-no

Author(s):

Hui Wang ◽

Ming-Hua Xu

Keyword(s):

Asymmetric Synthesis ◽

Arylboronic Acids ◽

Enantioselective Addition

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Chiral ligands for asymmetric synthesis: enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by chiral N-α-pyridylmethyl amino alcohols

Tetrahedron Letters ◽

10.1016/s0040-4039(00)01842-6 ◽

2000 ◽

Vol 41 (52) ◽

pp. 10263-10266 ◽

Cited By ~ 19

Author(s):

Hongying Yun ◽

Yangjie Wu ◽

Yusheng Wu ◽

Kuiling Ding ◽

Ying Zhou

Keyword(s):

Asymmetric Synthesis ◽

Aromatic Aldehydes ◽

Amino Alcohols ◽

Chiral Ligands ◽

Enantioselective Addition

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Rhodium-Catalyzed Highly Enantioselective Addition of Arylboronic Acids to Cyclic Aldimines: Practical Asymmetric Synthesis of Cyclic Sulfamidates

Synthesis ◽

10.1055/s-0033-1338418 ◽

2013 ◽

Vol 45 (15) ◽

pp. 2125-2133 ◽

Cited By ~ 26

Author(s):

Ming-Hua Xu ◽

Hui Wang

Keyword(s):

Asymmetric Synthesis ◽

Arylboronic Acids ◽

Enantioselective Addition

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ChemInform Abstract: Chiral N,N-Dialkylnorephedrines as Catalysts of the Highly Enantioselective Addition of Dialkylzincs to Aliphatic and Aromatic Aldehydes. The Asymmetric Synthesis of Secondary Aliphatic and Aromatic Alcohols of High Optical Purity.

ChemInform ◽

10.1002/chin.199146059 ◽

2010 ◽

Vol 22 (46) ◽

pp. no-no

Author(s):

K. SOAI ◽

S. YOKOYAMA ◽

T. HAYASAKA

Keyword(s):

Asymmetric Synthesis ◽

Optical Purity ◽

Aromatic Aldehydes ◽

High Optical Purity ◽

Aromatic Alcohols ◽

Enantioselective Addition

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Asymmetric synthesis with "privileged" ligands

Pure and Applied Chemistry ◽

10.1351/pac200173020325 ◽

2001 ◽

Vol 73 (2) ◽

pp. 325-329 ◽

Cited By ~ 13

Author(s):

Marco Bandini ◽

Pier Giorgio Cozzi ◽

Achille Umani-Ronchi

Keyword(s):

Open Access ◽

Asymmetric Synthesis ◽

Carbonyl Compounds ◽

Aromatic Aldehydes ◽

Redox Processes ◽

Asymmetric Allylation ◽

Salen Complexes ◽

Allyl Halides ◽

Different Types ◽

Enantioselective Addition

Different types of chiral "privileged" ligands 1 and 2 in promoting enantioselective addition of allylating agents to aliphatic and aromatic aldehydes are described. Here, a new concept in the asymmetric allylation reaction is presented. Redox [Cr (Salen) ] mediated addition of allyl halides to carbonyl compounds is described, and mechanistic investigations are discussed. These results open access to the fascinating area of the catalytic redox processes mediated by metallo-Salen complexes.

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