Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem‐Diborylalkanes by an Asymmetric Allylic Substitution DOI

Yeosan Lee,

Jinyoung Park, Seung Hwan Cho

и другие.

Angewandte Chemie, Год журнала: 2018, Номер 130(39), С. 13112 - 13116

Опубликована: Июль 2, 2018

Abstract We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X=Br, Cl) their application in synthesis enantioenriched gem ‐diborylalkanes bearing a stereogenic center at β‐position diboryl groups an asymmetric allylic substitution reaction. The reaction has broad substrate scope, various can be obtained good yields with excellent enantioselectivity. Further elaboration provides access to diverse set valuable chiral building blocks.

Язык: Английский

Iridium-Catalyzed Enantioselective Allyl–Allyl Cross-Coupling of Racemic Allylic Alcohols with Allylboronates DOI
Yu Zheng,

Bei-Bei Yue,

Kun Wei

и другие.

Organic Letters, Год журнала: 2018, Номер 20(24), С. 8035 - 8038

Опубликована: Дек. 3, 2018

Carreira's iridium-(P, olefin) phosphoramidite-based catalytic system that allows asymmetric allyl–allylboronate cross-coupling with high enantioselectivity is reported. This transformation tolerates a large variety of racemic branched allylic alcohols and allylboronate substrates. The utility the coupling demonstrated in concise synthesis (−)-preclamol.

Язык: Английский

Процитировано

25

Iridium-catalyzed enantioselective olefinic C(sp2)–H allylic alkylation DOI Creative Commons
Rahul Sarkar, Santanu Mukherjee

Chemical Science, Год журнала: 2021, Номер 12(8), С. 3070 - 3075

Опубликована: Янв. 1, 2021

The first iridium-catalyzed enantioselective allylic alkylation of an olefinic C(sp2)–H bond – that α,β-unsaturated carbonyl compound, is developed in cooperation with Lewis base catalysis.

Язык: Английский

Процитировано

20

Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp2)–H allylic alkylation of α,β-unsaturated carbonyls DOI Creative Commons
Sankash Mitra, Rahul Sarkar, Aditya Chakrabarty

и другие.

Chemical Science, Год журнала: 2022, Номер 13(42), С. 12491 - 12497

Опубликована: Янв. 1, 2022

Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp2)-H allylic alkylation of kojic acid and structurally related α,β-unsaturated carbonyl compounds is developed. This reaction, catalyzed by an Ir(i)/(P,olefin) complex, utilizes the nucleophilic character α-hydroxy carbonyls, to introduce allyl group at its β-position in a branched-selective manner good excellent yield with uniformly high enantioselectivity (up >99.9 : 0.1 er). To best our knowledge, this report represents first example use transition metal highly transformation.

Язык: Английский

Процитировано

13

Catalytic Enantioselective Synthesis of 1,4-Benzodioxepines DOI
Xi Zou,

Guangwu Sun,

Hai Huang

и другие.

Organic Letters, Год журнала: 2019, Номер 22(1), С. 249 - 252

Опубликована: Дек. 16, 2019

An efficient organocatalytic enantioselective synthesis of chiral 1,4-benzodioxepines is described. By proper incorporation an intramolecular oxetane desymmetrization process, a range benzylic alcohols bearing internal reacted in the presence suitable phosphoric acid catalyst to form with high enantioselectivity. This process provides new catalytic asymmetric example direct seven-membered heterocycles good stereocontrol.

Язык: Английский

Процитировано

21

Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem‐Diborylalkanes by an Asymmetric Allylic Substitution DOI

Yeosan Lee,

Jinyoung Park, Seung Hwan Cho

и другие.

Angewandte Chemie, Год журнала: 2018, Номер 130(39), С. 13112 - 13116

Опубликована: Июль 2, 2018

Abstract We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X=Br, Cl) their application in synthesis enantioenriched gem ‐diborylalkanes bearing a stereogenic center at β‐position diboryl groups an asymmetric allylic substitution reaction. The reaction has broad substrate scope, various can be obtained good yields with excellent enantioselectivity. Further elaboration provides access to diverse set valuable chiral building blocks.

Язык: Английский

Процитировано

20