Use of odorless thiols: Formal asymmetric Michael addition of hydrogen sulfide to α-substituted α,β-unsaturated carbonyl compounds

Organic Letters

Volumn 3, Issue 20, 2001, Pages 3121-3124

  Nishide, Kiyoharu ^a   Ohsugi, Shin ichi ^a   Shiraki, Hiroaki ^a   Tamakita, Hirokazu ^a   Node, Manabu ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

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EID: 0001581986     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016406d     Document Type: Article

References (29)

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21. (a) Nishide, K.; Shigeta, Y.; Obata, K.; Node, M. J. Am. Chem. Soc. 1996, 118, 13103-13104.
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24. (-)-10-Mercaptoisoborneol has almost no odor compared to other malodorous thiols. The syntheses and utility of other new odorless thiols and sulfides will be published elsewhere.
25. The diastereomeric excess of protonation depended on the dryness of the (-)-10-mercaptoisoborneol which was used after drying overnight over phosphorous pentoxide under high vacuum.
26. For example, the R-configuration at the α-position of the ester 2f was determined by comparison of the sign of the specific rotation of (R)-ethyl 2-methyl-3-phenylpropionate obtained by reductive desulfurization of 2f with Raney nickel with that in the literature: (a) Levene, P. A.; Marker, R. E. J. Biol. Chem. 1935, 110, 299-309.
27. (b) Cohen, S. G.; Milovanovic, A. J. Am. Chem. Soc. 1968, 90, 3495-3502.
28. (c) Jacques, J.; Gros, C.; Bourcier, S. Stereochemistry: Fundamentals and Methods; Georg Thieme Publishers: Stuttgart, 1977; Vol. 4, p 84, entry 1. An X-ray crystallographic analysis of (2S)-N-{3-[1R,2S,4S)-2-hydroxybornane-10-sulfenyl]-2-methylpropanoyl}-L-proline benzyl ester, an intermediate for the synthesis of the captopril derivative 6, showed the S-configuration at the α-position of the amide carbonyl, in which the enantiomer (+)-A was used (see Supporting Information).
29. Captopril is used in clinics as an orally active antihypertensive agent having a unique inhibitory action on the angiotensin-converting enzyme. Its derivative 6 was prepared from ent-5 which was obtained in this Michael addition of (+)-A derived from (-)-10-camphorsulfonic acid.