Michael addition to a chiral non-racemic 2-phosphono-2,3-didehydrothiolane S-oxide

Tetrahedron Asymmetry

Volumn 20, Issue 3, 2009, Pages 293-297

  Gulea, Mihaela ^a   Kwiatkowska, Małgorzata ^b   Łyzwa, Piotr ^b   Legay, Remi ^a   Gaumont, Annie Claude ^a   Kiełbasiński, Piotr ^b  

^a UNIVERSITÉ DE CAEN   (France)

^b CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

3 PARA TOLYLFULFANYL 2 [2' (5,5 DIMETHYL 1,3,2 DIOXAPHOSPHORINANYL)]THIOLANE 1 OXIDE; 3 PHENYLSULFANYL 2 [2' (5,5 DIMETHYL 1,3,2 DIOXAPHOSPHORINANYL)]THIOLANE 1 OXIDE; 3 TERT BUTYLSULFANYL 2 [2' (5,5 DIMETHYL 1,3,2 DIOXAPHOSPHORINANYL)]THIOLANE 1 OXIDE; NITROGEN DERIVATIVE; NUCLEOPHILE; PHENYLAMINO 2 [2' (5,5 DIMETHYL 1,3,2 DIOXAPHOSPHORINANYL)]THIOLANE 1 OXIDE; SULFUR DERIVATIVE; THIOPHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; MICHAEL ADDITION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY; THERMODYNAMICS; X RAY ANALYSIS;

EID: 62849092781     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.12.034     Document Type: Article

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12. 31P NMR spectrum of 1 shows two signals for a low ee (0-40%), while in the case of a moderate to high ee (65-95%) the signals overlap. This may explain why only one signal can be observed for some enantiomerically enriched samples of 1.
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15. The same procedure as for the preparation of (S)-(+)-2 was used. The starting phosphonothiolane was oxidized by (-)-8,8-dichloro-camphorsulfonyl-oxaziridine to give a non-racemic mixture of (-)-1/(+)-1 in about an 84:16 ratio. The mixture was enantioenriched in enantiomer (-)-1 by crystallization and substrate 1 having 90% ee was reacted with benzenethiol. The resulted adduct was recrystallized to afford an enantiopure sample of (R)-(-)-2.
16. See Section 4.2.1.
17. 3 as normally applied.