The stereospecific olefin formation reaction of 10-P-5 β-hydroxy- α,β-diphenylethylphosphoranes

Tetrahedron Letters

Volumn 38, Issue 44, 1997, Pages 7753-7756

  Kojima, Satoshi ^a   Kawaguchi, Kazuhiro ^a   Akiba, Kin Ya ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; LITHIUM DERIVATIVE; PHOSPHORANE DERIVATIVE; STILBENE DERIVATIVE; STILBENE OXIDE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; REDUCTION; STEREOSPECIFICITY;

EID: 0030666279     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10069-7     Document Type: Article

References (25)

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11. An independent study has revealed that when aryl groups are replaced with trifluoromethyl groups, olefin formation is observed in thermal reactions. Kawashima, T.; Watanabe, K.; Okazaki, R. Tetrahedron Lett. 1997, 38, 551-554.
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22. All diastereomers of 5 and 7 gave correct elemental analysis (within 0.4%) and reasonable spectra. Mp: 5-Sp*R*S* (203.5-204.5 °C, dec); 5-Sp*S*R* (200.5-201.5 °C, dec); 5-Sp*R*R* (165-165.5 °C, dec); 5-Sp*S*S* (196-197 °C, dec); 7-Sp*R* (160-161 °C, dec); 7-Sp*S* (189-190 °C, dec).
23. Details of the X-ray analysis will be reported later in a full account.
24. The X-ray structure of a stiboranide differing only in the pnictogen atom suggests TBP character. See: Akiba, K.-y.; Nakata, H.; Yamamoto, Y.; Kojima, S. Chem. Lett. 1992, 1559-1562.
25. The characteristic angular relationship of substituents within the epoxide would make this Ph group the most bulky in a ring opening reaction involving in-line attack of the P nucleophile.