Stereoselective synthesis of styrene oxides via a Mitsunobu cyclodehydration

Organic Letters

Volumn 3, Issue 16, 2001, Pages 2513-2515

  Weissman, Steven A ^a   Rossen, Kai ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; EPOXIDE; NEUROKININ 1 RECEPTOR; PHOSPHINE DERIVATIVE; STYRENE OXIDE; SUBSTANCE P;

ARTICLE; CHEMISTRY; CYCLIZATION; DRUG ANTAGONISM; SYNTHESIS;

CYCLIZATION; EPOXY COMPOUNDS; INDICATORS AND REAGENTS; PHOSPHINES; RECEPTORS, NEUROKININ-1; SUBSTANCE P;

EID: 0035833732     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016167u     Document Type: Article

References (26)

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24. This stereospecific outcome is consistent with the Mitsunobu cyclodehydration of propane-1,2-diol, which also gave 82-85% retention of configuration. See ref 10. Retention should also be favored here on the basis of steric considerations as the least hindered alcohol of vicinal diols is typically activated.
25. Standard Conditions. The phosphine (1.5 equiv) was combined with the solvent (1.3 M) at 5 °C. followed by dropwise addition of the DIAD (1.45 equiv) and warming to 15 °C. After aging for 15 min, the solution was cooled to 5-10 °C and the diol was added (1 M in the solvent), followed by warming to room temperature. Reactions were typically complete within 2 h at 25-40 °C.
26. Ethyl acetate showed low conversion in the standard reaction.