Alkylation of lithiated dimethyl tartrate acetonide with unactivated alkyl halides and application to an asymmetric synthesis of the 2,8-dioxabicyclo[3.2.1]octane core of squalestatins/zaragozic acids

Alkylation of lithiated dimethyl tartrate acetonide with unactivated alkyl halides and application to an asymmetric synthesis of the 2,8-dioxabicyclo[3.2.1]octane core of squalestatins/zaragozic acids

(R,R)-Dimethyl tartrate acetonide 7 in THF/HMPA undergoes deprotonation with LDA and reaction at −78 °C during 12–72 h with a range of alkyl halides, including non-activated substrates, to give single diastereomers (at the acetonide) of monoalkylated tartrates 17, 24, 33a–f, 38a,b, 41 of R,R-configu...

Detaylı Bibliyografya
Asıl Yazarlar:	Sintim, H, Al Mamari, H, Almohseni, H, Fegheh-Hassanpour, Y, Hodgson, D
Materyal Türü:	Journal article
Baskı/Yayın Bilgisi:	Beilstein-Institut 2019

Benzer Materyaller

Alkylation of lithiated dimethyl tartrate acetonide with unactivated alkyl halides and application to an asymmetric synthesis of the 2,8-dioxabicyclo[3.2.1]octane core of squalestatins/zaragozic acids
Yazar:: Herman O. Sintim, ve diğerleri
Baskı/Yayın Bilgisi: (2019-05-01)

Synthetic studies toward the Zaragozic agios (squalestatins).
Yazar:: Villalonga-Barber, C, ve diğerleri
Baskı/Yayın Bilgisi: (2000)

Alkene ozonolysis in the presence of diazo functionality: accessing an intermediate for squalestatin synthesis
Yazar:: Almohseni, HAA, ve diğerleri
Baskı/Yayın Bilgisi: (2019)

Selectivity in the cycloadditions of carbonyl ylides with glyoxylates: an approach to the zaragozic acids-squalestatins
Yazar:: Hodgson, D, ve diğerleri
Baskı/Yayın Bilgisi: (2000)

Alkyl-Alkyl Suzuki Cross-Coupling of Unactivated Secondary Alkyl Chlorides
Yazar:: Lu, Zhe, ve diğerleri
Baskı/Yayın Bilgisi: (2013)

Stereoconvergent Amine-Directed Alkyl–Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides
Yazar:: Lu, Zhe, ve diğerleri
Baskı/Yayın Bilgisi: (2013)

Studies towards a stereocontrolled synthesis of the tricarboxylate core of the zaragozic acids-squalestatins by a cycloaddition-rearrangement strategy
Yazar:: Hodgson, D, ve diğerleri
Baskı/Yayın Bilgisi: (2000)

Cross-coupling reactions of unactivated alkyl halides
Yazar:: Zhou, Jianrong (Jianrong Steve)
Baskı/Yayın Bilgisi: (2006)

2-Alkylation of 3-Alkyindoles With Unactivated Alkenes
Yazar:: Xuling Pan, ve diğerleri
Baskı/Yayın Bilgisi: (2022-02-01)

Development of Barbier-Grignard-type alkylation reaction using unactivated alkyl halides in water.
Yazar:: Shen, Zhi Liang.
Baskı/Yayın Bilgisi: (2008)

Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins
Yazar:: Owston, Nathan A., ve diğerleri
Baskı/Yayın Bilgisi: (2013)

Facile and general electrochemical deuteration of unactivated alkyl halides
Yazar:: Pengfei Li, ve diğerleri
Baskı/Yayın Bilgisi: (2022-06-01)

Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides
Yazar:: Yi Fang, ve diğerleri
Baskı/Yayın Bilgisi: (2018-06-01)

Evolution of a cycloaddition-rearrangement approach to the squalestatins: a quarter-century odyssey
Yazar:: Almohseni, HAA, ve diğerleri
Baskı/Yayın Bilgisi: (2020)

Intramolecular Heck couplings of unactivated alkyl electrophiles : synthetic and mechanistic studies
Yazar:: Firmansjah, Luke
Baskı/Yayın Bilgisi: (2008)

Enantioselective alkylative cross-coupling of unactivated aromatic C–O electrophiles
Yazar:: Zishuo Zhang, ve diğerleri
Baskı/Yayın Bilgisi: (2022-05-01)

Pd-catalyzed formal Mizoroki–Heck coupling of unactivated alkyl chlorides
Yazar:: Geun Seok Lee, ve diğerleri
Baskı/Yayın Bilgisi: (2021-02-01)

Chlorine Atom Transfer of Unactivated Alkyl Chlorides Enabled by Zirconocene and Photoredox Catalysis
Yazar:: Toshimasa Okita, ve diğerleri
Baskı/Yayın Bilgisi: (2023-02-01)

Regioselective Ni-Catalyzed reductive alkylsilylation of acrylonitrile with unactivated alkyl bromides and chlorosilanes
Yazar:: Jinwei Sun, ve diğerleri
Baskı/Yayın Bilgisi: (2022-11-01)

Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO2
Yazar:: Guo-Quan Sun, ve diğerleri
Baskı/Yayın Bilgisi: (2021-12-01)

Nickel-catalyzed reductive coupling of homoenolates and their higher homologues with unactivated alkyl bromides
Yazar:: Tingzhi Lin, ve diğerleri
Baskı/Yayın Bilgisi: (2020-11-01)

A diastereocontrolled synthesis of perseitol using a dioxabicyclo[3.2.1]octane chiral building block
Yazar:: Kohei Kadota, ve diğerleri
Baskı/Yayın Bilgisi: (2003-08-01)

Squarate desymmetrisation–ozonolysis as an approach to β-substituted-α-ketosuccinates and squalestatin synthesis
Yazar:: Sintim, H, ve diğerleri
Baskı/Yayın Bilgisi: (2019)

Protocol for iron-catalyzed cross-electrophile coupling of aryl chlorides with unactivated alkyl chlorides
Yazar:: Pengjie Xian, ve diğerleri
Baskı/Yayın Bilgisi: (2024-03-01)

Enantioconvergent Cross-Couplings of Racemic Alkylmetal Reagents with Unactivated Secondary Alkyl Electrophiles: Catalytic Asymmetric Negishi α-Alkylations of N-Boc-Pyrrolidine
Yazar:: Cordier, Christopher J., ve diğerleri
Baskı/Yayın Bilgisi: (2018)

New Directing Groups for Metal-Catalyzed Asymmetric Carbon–Carbon Bond-Forming Processes: Stereoconvergent Alkyl–Alkyl Suzuki Cross-Couplings of Unactivated Electrophiles
Yazar:: Wilsily, Ashraf, ve diğerleri
Baskı/Yayın Bilgisi: (2013)

Ni-catalyzed enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohols and aryl bromides
Yazar:: Li-Li Zhang, ve diğerleri
Baskı/Yayın Bilgisi: (2024-03-01)

Direct C(sp2)–H alkylation of unactivated arenes enabled by photoinduced Pd catalysis
Yazar:: Daeun Kim, ve diğerleri
Baskı/Yayın Bilgisi: (2020-10-01)

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions
Yazar:: Martyn Jevric, ve diğerleri
Baskı/Yayın Bilgisi: (2024-04-01)

Synthesis of (−)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition–rearrangement and cross-electrophile coupling
Yazar:: Fegheh-Hassanpour, Y, ve diğerleri
Baskı/Yayın Bilgisi: (2017)

Nickel-Catalyzed Carbon–Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations
Yazar:: Fu, Gregory C., ve diğerleri
Baskı/Yayın Bilgisi: (2014)

Synthesis and coordination ability of tartrate-derived N-alkyl dicarbohydrazides towards Cu2+ ions
Yazar:: Jana Kousalová, ve diğerleri
Baskı/Yayın Bilgisi: (2012-09-01)

Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon–Boron Bonds
Yazar:: Dudnik, Alexander S., ve diğerleri
Baskı/Yayın Bilgisi: (2013)

Author Correction: Direct C(sp2)–H alkylation of unactivated arenes enabled by photoinduced Pd catalysis
Yazar:: Daeun Kim, ve diğerleri
Baskı/Yayın Bilgisi: (2020-11-01)

Migratory functionalization of unactivated alkyl bromides for construction of all-carbon quaternary centers via transposed tert-C-radicals
Yazar:: Chuan Zhu, ve diğerleri
Baskı/Yayın Bilgisi: (2020-09-01)

A cycloaddition-rearrangement approach to the squalestatins
Yazar:: Hodgson, D, ve diğerleri
Baskı/Yayın Bilgisi: (1996)

Recent Advances in the Nickel-Catalyzed Alkylation of C-H Bonds
Yazar:: Franc Požgan, ve diğerleri
Baskı/Yayın Bilgisi: (2024-04-01)

Nickel-catalyzed Suzuki-Miyaura reactions of unactivated halides with alkyl boranes and planar-chiral borabenzene catalysts for Diels-Alder reactions
Yazar:: Lu, Zhe
Baskı/Yayın Bilgisi: (2011)

Enantioselective bifunctional iminophosphorane catalyzed sulfa-Michael addition of alkyl thiols to unactivated β-substituted-α,β-unsaturated esters
Yazar:: Yang, J, ve diğerleri
Baskı/Yayın Bilgisi: (2016)

In situ copper photocatalysts triggering halide atom transfer of unactivated alkyl halides for general C(sp3)-N couplings
Yazar:: Hang Luo, ve diğerleri
Baskı/Yayın Bilgisi: (2024-07-01)