Enantioselective Iridium‐Catalyzed Allylation of Acetylenic Ketones via 2‐Propanol‐Mediated Reductive Coupling of Allyl Acetate: C14‐C23 of Pladienolide D

AbstractCarbonyl allylation reactions constitute an important step in the formation of carbon–carbon reactions, and involve various related reactions that chiefly use allylmetal reagents. This report presents a nickel-catalyzed carbonyl allylation reaction using allyl acetate, which produces homoallyl alcohols in moderate to good yields, as an efficient methodology under reductive coupling conditions.

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Enantioselective Iridium‐Catalyzed Allylation of Acetylenic Ketones via 2‐Propanol‐Mediated Reductive Coupling of Allyl Acetate: C14‐C23 of Pladienolide D

Angewandte Chemie ◽

10.1002/ange.201908939 ◽

2019 ◽

Vol 131 (52) ◽

pp. 18979-18983

Author(s):

Gilmar A. Brito ◽

Woo‐Ok Jung ◽

Minjin Yoo ◽

Michael J. Krische

Keyword(s):

Reductive Coupling ◽

Allyl Acetate

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Reductive coupling of 4,5-ethylenedithio-1,3-diselenol-2-one

ChemSpider Synthetic Pages ◽

10.1039/sp421 ◽

2010 ◽

Author(s):

Nikola Paul Chmel

Keyword(s):

Reductive Coupling

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Homopolymerization and Copolymerization of Alkenyldichlorosilanes by Reductive Coupling

10.21236/ada206214 ◽

1989 ◽

Author(s):

H. K. Kim ◽

K. Matyjaszewski

Keyword(s):

Reductive Coupling

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Metal-free Reductive Coupling of Biphenyl Tosylhydrazones with Phenols or Benzyl Alcohols

Letters in Organic Chemistry ◽

10.2174/1570178614666170608084019 ◽

2017 ◽

Vol 14 (10) ◽

Author(s):

Yang Liu ◽

Ping Liu ◽

Yan Liu ◽

Yu Wei ◽

Bin Dai

Keyword(s):

Reductive Coupling ◽

Benzyl Alcohols ◽

Metal Free

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Photoreaction of N-butyl 3,4-dimethoxy-6-nitrobenzamide with butylamine. A model study for lysine-directed photoaffinity labelling

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19871780 ◽

1987 ◽

Vol 52 (7) ◽

pp. 1780-1785 ◽

Cited By ~ 3

Author(s):

Petr Kuzmič ◽

Libuše Pavlíčková ◽

Milan Souček

Keyword(s):

Nitro Group ◽

Aromatic Ring ◽

Ultraviolet Irradiation ◽

Title Compound ◽

Reductive Coupling ◽

Photoaffinity Labelling ◽

Photolysis Rate ◽

Model Study ◽

A Minor

Ultraviolet irradiation of the title compound I in the presence of butylamine gave predominantly products of nucleophilic photosubstitution by the amine, i.e., nitroanilines IIa and IIb. Besides, small amounts of products of hydrolysis (phenol III) and reductive coupling (azoxybenzene IV) were also formed. Comparison of the overall photolysis rate of I with that of 3,4-dimethoxy-1-nitrobenzene (V) indicates a minor loss of reactivity, most probably due to some deviation from coplanarity of the activating nitro group and the aromatic ring.

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