Stereoselective addition of phenyl selenyl chloride to methoxy alkenes derived from N-protected chiral α-amino acids.

Demarcus, Mariangela; Filigheddu, Silvia N.; Mann, André; Taddei, Maurizio

doi:10.1016/s0040-4039(99)00761-3

Cited by 16 publications

(4 citation statements)

References 7 publications

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“…Phenylselenyl chloride has been added stereoselectively to methoxyalkenes 1 derived from N-protected chiral amino acids (Scheme 1). 3 The aldehydes 2 thus obtained could be transformed into aziridinecarboxylic acids 3 in good yield by treatment with MCPBA in the presence of sodium carbonate.…”

Section: Three-membered Ringsmentioning

confidence: 96%

Saturated nitrogen heterocycles

Mitchenson

Nadin

2000

J. Chem. Soc., Perkin Trans. 1

200

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Section: Three-membered Ringsmentioning

confidence: 96%

Saturated nitrogen heterocycles

Mitchenson

Nadin

2000

J. Chem. Soc., Perkin Trans. 1

200

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“…(E)-Methoxy alkenes derived from N-Boc or N-Cbzamino acids undergo stereoselective addition of phenyl selenyl chloride in the presence of Ti(O-i Pr) 4 and LiCl to give the corresponding phenylselenyl aldehydes [28]. The Rayner developed the synthetic approach to novel enantio-merically pure selenides derived from (+)-camphor and (-)-camphor-10-sulfonate esters [29].…”

Section: Based On Achiral Organoselenium Compoundsmentioning

confidence: 99%

Asymmetric Synthesis of Chiral Organoselenium Compounds

Chengjian¹,

Huang²

2006

COC

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Chiral organoselenium compounds can be attained from three types of asymmetric synthesis. Chiral substratecontrolled methods, chiral auxiliary-controlled methods, and chiral catalyst-controlled methods toward optically active organoselenium derivatives were illustrated. The strategy and classification of methods underlying all asymmetric synthesis therefore involve enantiomerically pure compounds to influence the stereochemical outcome of the reactions. In this review, the advances in asymmetric synthesis of some important classes of chiral organoselenium compounds were described. A. INTRODUCTIONThe asymmetric synthesis of optically active organoselenium compounds constitutes engaging fundamental problems in both scientific research and drug discovery [1]. Over past several years, chiral organoselenium compounds have received a new impetus in the preparations, developments, and asymmetric transformations. The development of stereoselective reactions to form C-Se, Se-Se, Se-O, Sehalogen, Se-N bonds has witnessed the burgeoning levels of diversity, efficiency and applicability [2]. Different chiral selenoorganic functional groups and reagents could be easily synthesized in various means. Optically active diselenides,arylseleno alcohols, -oxo--seleno esters, oxaselenazoles, selenoxides, seleninamides and selenonium ylides were obtained and utilized for some facile transformations, in which these chiral motifs play the critical roles in controlling both the course of the reaction and the stereoselectivity for the specific structural and electronic features [3]. In this review, the recent progress of synthetic methods for some important classes of chiral organoselenium compounds are described. We illustrate three types of asymmetric synthesis according to how the enantiomerically pure compound is used, excluding those processes that involve the derivatization of a reagent without creating any new stereogenic element. The known methods which have been used in asymmetric synthesis of chiral organoselenium compounds are classified into three types:(i) chiral substrate-controlled methods;(ii) chiral auxiliary-controlled methods; (iii) chiral catalyst-controlled methods. B. CHIRAL SUBSTRATE-CONTROLLED METHODSThe chiral substrate-controlled methods may be represented as Equation 1, the influence of an adjacent stereogenic group (X*) involves the formation of a new

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“…(E)-Methoxy alkenes derived from α-amino acids undergo selenenylation to give the corresponding α-phenylselanyl aldehydes in good yield and with good diastereoselectivity (Scheme 66). 129 Finally, direct amino-phenylselenenylation of α,β-unsaturated esters has been achieved using benzeneselenenyl chloride, activated by a Lewis acid, and in the presence of a primary amine (Scheme 67). 130 Treatment of the product α-phenylseleno β-amino esters with tert-butyllithium gives α-phenylseleno β-lactams apparently via the cyclisation of a dianionic intermediate.…”

Section: Functionalised Sulfides and Selenidesmentioning

confidence: 99%

The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones

Procter¹

2000

J. Chem. Soc., Perkin Trans. 1

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Stereoselective addition of phenyl selenyl chloride to methoxy alkenes derived from N-protected chiral α-amino acids.

Cited by 16 publications

References 7 publications

Saturated nitrogen heterocycles

Saturated nitrogen heterocycles

Asymmetric Synthesis of Chiral Organoselenium Compounds

The synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones

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