Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System

Zhang, Wei; Chen, Jingchao; Zeng, Guang‐Zhi; Yang, Fan; Xu, Jiaxi; Sun, Weiqing; Shinde, Madhuri Vikas; Fan, Baomin

doi:10.1021/acs.joc.6b03038

Cited by 29 publications

(10 citation statements)

References 46 publications

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“…The same group also described asymmetric ring opening reactions of aza-and oxabenzonorbornadienes 35, 218, 224 with aryl boronic acids 265 by using a Zn/Pd dual catalyst system [124]. As shown in Scheme 89, a combination of 10 mol% of Zn(OTf) 2 , 6 mol% of (R)-BINAP and 5 mol% of Pd(OAc) 2 was applied to promote these reactions which delivered a wide variety of chiral hydronaphthalene products 266 in homogeneous high yields (86-99%) and good to excellent enantioselectivities (72-99% ee).…”

Section: Ring-opening Reactionsmentioning

confidence: 99%

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Recent developments in enantioselective zinc-catalyzed transformations

Pellissier

2021

Coordination Chemistry Reviews

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This review collects the recent advances in the field of enantioselective zinc-catalyzed transformations, covering the literature since the beginning of 2015, illustrating the power of chiral green zinc catalysts to promote all types of reactions. A range of highly enantioselective reactions have been developed in the last six years, including cycloadditions, alkynylation/allylation reactions of carbonyl compounds and derivatives, additions of diorganozincs to carbonyl compounds and derivatives, Mannich reactions, (nitro)aldol reactions, other 1,2-nucleophilic additions to carbonyl compounds and derivatives, Michael additions, Friedel-Crafts reactions, reductions, a-functionalizations of carbonyl compounds, ringopening reactions, epoxidations, halolactonizations, domino/tandem reactions and miscellaneous reactions.

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Section: Ring-opening Reactionsmentioning

confidence: 99%

“…Scheme 89. Ring-opening reaction of oxa-and azabenzonorbornadienes with aryl boronic acids in the presence of a dual Zn/Pd catalyst system[124].Scheme 90. Ring-opening reaction of oxa-and azabenzonorbornadienes with aromatic oximes in the presence of a dual Zn/Pd catalyst system[125].…”

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confidence: 99%

Recent developments in enantioselective zinc-catalyzed transformations

Pellissier

2021

Coordination Chemistry Reviews

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“…Quite recently, Fan and co‐workers reported a highly active palladium/zinc co‐catalytic system working in neutral reaction conditions without the necessity of a base that was suitable for both oxa‐ and azabenzonorbornadienes [59] . While the ring opening reaction of bicyclic oxazines (i.e 3‐aza‐2‐oxabicyclo[2.2.1]heptenes) with arylboronic acids has been developed only in a racemic fashion using rhodium(I) catalysis, [60] the chemistry of the ring opening of bicyclic hydrazines (i.e 2,3‐diazabicyclo[2.2.1]heptenes) has been studied in much more detail.…”

Section: Boronic Acids and Derivativesmentioning

confidence: 99%

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Pineschi

2021

Adv Synth Catal

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The particular nature of boron compounds allows an ample modularity of their properties ranging from Lewis acids, C‐nucleophiles, B‐nucleophiles, or even conjunctive reagents for new synthetic manipulations. Moreover, the increasing demand for functionalized boron derivatives for pharmaceutical or material science applications requires the development of new synthetic methods for boron introduction in organic compounds. This review summarizes the possible combinations of boron derivatives with a variety of strained heterocycles reported in the most recent literature.

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“…Both aliphatic and aromatic alcohols were found to be suitable hydrogen source giving the corresponding enantiomerically enriched 1,2‐dihydronaphth‐1‐ol products in good to high yields with excellent enantioselectivity. The highly active co‐catalytic system of Pd(OAc) 2 and Zn(OTf) 2 was also used for the ring‐opening reaction of oxa/azabicyclic alkenes with boronic acids in the presence of ( R )‐BINAP in THF . The chiral 1,2‐dihydronaphthalene products were obtained in high yields and high enantioselectivity (up to 98 % ee ).…”

Section: Palladium/lewis Acid Co‐catalyzed Ring‐opening Reactionmentioning

confidence: 99%

Transition Metal/Lewis Acid Co‐Catalyzed Ring‐Opening Reactions of Oxa/Azabenzonorbornadienes

Zhang¹,

Khan

Fan

2020

ChemistrySelect

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The transition metal catalyzed ring-opening reactions of oxa/ azabenzonorbornadienes have emerged as one of the important methods for the synthesis of structural framework of biological importance bearing multiple functional groups. The reactions are catalyzed by transition metals such as Pd, Ir, Rh, Cu, Co, Pt, Ru, etc. Pioneered by Lautens et. al, it was realized that Lewis acids (LA) can play an important role in the ring-opening reaction and hence enhance both the reaction yield and stereo/regioselectivity of the products. They act as an activator/co-catalyst in the ring-opening reaction. In this review, we present an overview of the transition metal/Lewis acid co-catalyzed ring-opening reactions of oxa/azabenzonorbornadienes with different nucleophiles leading to the formation of different ring-opening products.

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Asymmetric Ring-Opening Reactions of Aza- and Oxa-bicyclic Alkenes with Boronic Acids Using a Palladium/Zinc Co-catalytic System

Cited by 29 publications

References 46 publications

Recent developments in enantioselective zinc-catalyzed transformations

Recent developments in enantioselective zinc-catalyzed transformations

Boron Reagents and Catalysts for the Functionalization of Strained Heterocycles

Transition Metal/Lewis Acid Co‐Catalyzed Ring‐Opening Reactions of Oxa/Azabenzonorbornadienes

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