Stereocontrol in [4+2]Type Cycloaddition of an Aldimine Derived from (S)-Ethyl Lactate with 2-Siloxy-1,3-butadienes

Ishimaru, Kaori; Watanabe, Kazutaka; Yamamoto, Yohsuke; Akiba, Kin‐ya

doi:10.1055/s-1994-22902

Cited by 19 publications

(1 citation statement)

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“…In 1994, Akiba reported the incorporation of tbutyldimethylsilyl(TBS)-protected chiral alcohols in the auxiliary could induce diastereoselectivity for the resulting cycloadduct [18]. The imines were prepared from benzylamine and TBS-protected (S)-ethyl lactate (Scheme 3).…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Aza-Diels-Alder Reactions

Rowland¹,

Rowland²,

Zhang³

et al. 2006

COC

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The Diels-Alder reaction is one of the most useful and often studied transformations in organic chemistry. The reaction has been employed, often as the key step, in the total synthesis of a wide range of biologically-active natural products. The utility of the reaction is based upon its ability to form six-membered cyclic systems with up to four contiguous stereocenters as well as the reactions ability to incorporate heteroatoms into the cycloadduct. The use of imines as the dienophile has been studied in great detail over the last fifteen years. The development of stereoselective variants of the reaction has been at the forefront of these studies. The use of chiral auxiliaries and chiral catalyst to control the stereochemistry of the product has seen much success over this period of time. The purpose of this review is to give a detailed discussion of the recent advances in Diels-Alder methodology involving a carbon-nitrogen double bond. The review is divided into two major sections. The first discusses the development of Diastereoselective aza-Diels-Alder reactions, while the second part discusses Enantioselective variants of the reaction.

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Section: Introductionmentioning

confidence: 99%

Stereoselective Aza-Diels-Alder Reactions

Rowland¹,

Rowland²,

Zhang³

et al. 2006

COC

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Diels‐Alder Reactions of Imino Dienophiles

et al. 2005

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In comparison to all carbon [4 + 2] cycloadditions, Diesl‐Alder reactions are still in their infancy. The last four decades, however, have seen intensive research in this area. The results if that synthetic organic chemists now have a powerful tool at their disposal for rapid construction of highly functionalized six‐membered nitrogen heterocycles, often in a regio‐, diastereo‐, and enantioselective manner. This chapter encompasses the topic of imine[4 + 2] cycloaddition reactions, of which there are a number of variants. This chapter is limited exclusively to imine and iminium ion dienophiles that undergo inter‐ and intramolecular Diels‐Alder reactions with acylic and cyclic all‐carbon 1,3‐dienes affording 1,2,5,6‐tetrahydropyridines as the initial cycloadducts. In situations where there is a mechanistic ambiguity, such as reactions that proceed via Mannich reactions, these mechanisms are included since it is difficult to know where to draw the line on coverage. A comprehensive discussion of each structural type of imino dienophiles covers the literature up to the middle of 2004. A general overview of mechanistic, regiochemical, and sterochemical considerations is also presented. Specific relevant exo/endo issues, remote diasteroselectivity and the use of chiral auxiliaries are discussed under each separate imine type. Separate sections have also been included that describe intramolecular reactions, as well as more recent advances in enantioselective cycloadditions involving chiral catalysts.

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Formation of Alkenes by Diels–Alder Reactions

Larock

2018

Comprehensive Organic Transformations

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General Reviews Regioselectivity Exo / Endo Selectivity Asymmetric Diels–Alder Reaction Mechanism Use of High Pressure Microwave Irradiation Infrared Irradiation Mechanical Ball Milling Ultracentrifugation Use of Ultrasound Catalysis Solvent Effects Cavity Effects Retro‐Diels–Alder Reaction Intramolecular Diels–Alder Reaction Inverse Electron‐Demand Diels–Alder Reaction Radical Cation Diels–Alder Reaction Ionic Diels–Alder Reaction Use of Heterodienophiles Use of Heteroatom‐Containing “Dienes” Use of Substituted 1,3‐Dienes o ‐Quinodimethanes and Heterocyclic Analogues Arynes and Hetarynes Some Other Dienophiles Dienophile Equivalents Transition Metal Carbenes as Dienophiles

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Stereocontrol in [4+2]Type Cycloaddition of an Aldimine Derived from (S)-Ethyl Lactate with 2-Siloxy-1,3-butadienes

Cited by 19 publications

References 0 publications

Stereoselective Aza-Diels-Alder Reactions

Stereoselective Aza-Diels-Alder Reactions

Diels‐Alder Reactions of Imino Dienophiles

Formation of Alkenes by Diels–Alder Reactions

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