Enantioselectivity of the Transfer of Hydrogen Atoms to Acyclic Prochiral Carbon-Centred Radicals Using Chiral Tin Hydrides

Schwarzkopf, Kay; Blumenstein, Michael; Hayen, Ahlke; Metzger, Jürgen O.

doi:10.1002/(sici)1099-0690(199801)1998:1<177::aid-ejoc177>3.0.co;2-z

Cited by 40 publications

(14 citation statements)

References 9 publications

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“…Alternatively, chiral tin hydrides bearing 2-(1-dimethylaminoalkyl)phenyl ligands have been employed as shown in Scheme 28. 34 Hydrides with chiral ligands such as 102 are hydrogen atom donors that have the potential to trap radicals enantioselectively. This has been investigated in the reduction of a-bromoester 103, where reaction with a 4:1 mixture of (inseparable) diastereomers of hydride 102 produced the (S)-enantiomer 104 in 34% yield and the (R)-enantiomer 105 in 28% yield.…”

Section: Reagent-controlled Enantioselective Reactionsmentioning

confidence: 99%

Stereoselective radical reactions

2003

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For many years, the reputed lack of selectivity in some free-radical reactions has resulted in this class of reaction being overlooked in the stereoselective synthesis of important target molecules. More recently, however, the situation has changed as new and milder methods of radical generation have been developed, which have helped researchers to gain a better understanding of the key factors that influence selectivity in radical transformations. As a consequence, the use of radicals in stereoselective synthesis is increasing and there are a number of important intra- and intermolecular additions, where high levels of stereoselectivity have been achieved in the formation of carbon-carbon bonds.

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Section: Reagent-controlled Enantioselective Reactionsmentioning

confidence: 99%

Stereoselective radical reactions

2003

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“…In recent years there has been increased interest in the synthesis of chiral organotin hydrides as enantioselective free radical reducing agents. [1][2][3][4][5][6][7] Only a small number of chiral organotin hydrides have been synthesized previously. Even fewer chiral organotin hydrides containing potentially intramolecular coordinating groups have been described.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of chiral organotin hydrides containing menthyl and oxazoline substituents†

Dakternieks

Dunn

Schiesser

et al. 2000

J. Chem. Soc., Dalton Trans.

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“…26 Accordingly, α-bromo-3-phenylpropionic acid 1d was synthesized by treating phenylalanine 8 with sodium nitrite in a HBr/KBr solution (eqn (2), Scheme 2), 27 while bromination of acids 9 and 10 carried out with NBS in CCl 4 gave rise to the formation of the corresponding α-bromo acids 1h,i in high yields (eqn ( 3) and (4), Scheme 2). 28…”

Section: Synthesis Of the Starting Materialsmentioning

confidence: 99%

Regioselective multicomponent sequential synthesis of hydantoins

et al. 2012

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The development of new practical and green methods for the synthesis of small heterocycles is an attractive area of research due to the well-known potential of heterocyclic small molecule scaffolds in the drug discovery process. Herein we report a one-pot, three-component sequential procedure for the synthesis of diversely 1,3,5- and 1,3,5,5-substituted hydantoins, in high yields and very mild conditions, using readily accessible starting materials such as azides, iso(thio)cyanates and substituted α-halo-acetic carboxylic acids. This methodology is especially convenient for the synthesis of spiro-hydantoins, which are particularly interesting bioactive compounds in medicinal chemistry.

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Enantioselectivity of the Transfer of Hydrogen Atoms to Acyclic Prochiral Carbon-Centred Radicals Using Chiral Tin Hydrides

Cited by 40 publications

References 9 publications

Stereoselective radical reactions

Stereoselective radical reactions

Synthesis of chiral organotin hydrides containing menthyl and oxazoline substituents†

Regioselective multicomponent sequential synthesis of hydantoins

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