- Diastereoselective addition of methylmetal reagents to 2-methylaldehydes
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The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-butyl moiety of high diastereomeric purity is described. These compounds can serve as potential building blocks for the preparation of several kinds of natural products. The diastereoselective addition of a number of methylmetal derivatives to three 3-substituted 2-methylaldehydes in various solvents was studied. An excellent diastereomeric ratio (95:5 anti-Cram/Cram) was obtained with 2-methyl-3-(phenylsulfanyl)propanal (5) and Me2Zn in the presence of TiCl4.
- Larsson, Michael,H?gberg, Hans-Erik
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- Copper-Catalyzed Stereospecific Hydroboration of Internal Allylic Alcohols
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An effective Cu-catalyzed stereospecific hydroboration of aliphatic and aromatic 1,1,2-trisubstituted internal allylic alcohols has been reported. This reaction proceeds via a silyl ether transient protection of allylic alcohols and subsequent stereospecific hydroboration. Followed by an oxidative workup, an array of acyclic, cyclic, and heterocyclic 1,3-diols was synthesized in good to excellent yields with good functional group tolerance and excellent diastereomeric ratios (> 20:1).
- Ji, Enhui,Meng, Haiwen,Zheng, Yue,Ramadoss, Velayudham,Wang, Yahui
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supporting information
p. 7367 - 7371
(2019/11/22)
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- Poly(phosphoric acid) (PPA)-Promoted 5- exo -Cyclization of Iminium Ions Generated in Situ: A Facile Access to Functionalized Indene Derivatives
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A metal-free Bronsted acid promoted two-component reaction between cinnamaldehydes and sulfonamides is described. This cascade process provides a simple and atom-economical alternative synthesis of a range of functionalized indenes from easily available starting materials. The resulting N -indenylsulfonamides were readily converted into the corresponding indenylenamines or indanones.
- Zhu, Yi-Fan,Geng, Xin-Le,Guan, Yong-Hong,Teng, Wei,Fan, Xiaohui
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supporting information
p. 1821 - 1827
(2017/09/30)
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- Assembly of indenamine derivatives through in situ formed N-sulfonyliminium ion initiated cyclization
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An expedient route to structurally diverse indenamine derivatives through condensation of the readily accessible substituted cinnamylaldehydes and sulfonylamines under the catalysis of FeCl3 has been developed, featuring high efficiency in the generation of two bonds and one ring in a single-step and water as the only by-product. This journal is the Partner Organisations 2014.
- Fan, Xiaohui,Lv, Hao,Guan, Yong-Hong,Zhu, Hong-Bo,Cui, Xiao-Meng,Guo, Kun
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supporting information
p. 4119 - 4122
(2014/04/03)
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- Secondary amine catalyzed retro-aldol reactions of enals and enones: One-pot conversion of enals to α-substituted derivatives
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A practical synthetic procedure to hydrolytically cleave the C,C-double bond of α,β-unsaturated aldehydes and ketones has been developed. Secondary amines are employed as organocatalysts for the retro-aldol process under simple and mild reaction conditions. Beside the generation of the parent aromatic aldehydes, the synthetic procedure has been successfully used in a one-pot reaction sequence to convert simple cinnamaldehydes into their α-aryl/alkyl substituted derivatives.
- Enders, Dieter,Nguyen, Thanh V.
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experimental part
p. 2091 - 2095
(2012/07/14)
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