π-Facial diastereoselectivity in the [4+2] cycloaddition of singlet oxygen as a mechanistic probe

Accounts of Chemical Research

Volumn 29, Issue 6, 1996, Pages 275-283

  Adam, Waldemar ^a,c,d,e   Prein, Michael ^a,b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b EMORY UNIVERSITY   (United States)

^c UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^d MIT

^e UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000929216     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar950164y     Document Type: Article

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135. It was pointed out by a reviewer that the observed regioselectivity in the photooxygenation of the 13q substrate contradicts the mechanistic concept of the hydroxy-directing effect because an attractive interaction between the hydroxy group and the incoming singlet oxygen dienophile should manifest itself in an increased reaction rate such that the preferred endoperoxidation should occur at the hydroxyethyl- rather than the observed methyl-substituted ring However, it should be kept in mind that the reactivity of singlet oxygen is characterized by a high sensitivity to steric and electronic effects of the reacting π system. For example, it is well documented (cf. refs 10 and 17a) that any allylic oxygen substituent markedly decreases the rate of singlet oxygen reactions through its inductive effect. The hydroxyethyl-substituted naphthalene ring will, therefore, possess a significantly lower reactivity than the alkylated one, and the hydroxy group, although decisive in dictating the diastereoselectivity, is incapable of counteracting the inherent lower reactivity of the hydroxyethyl-substituted benzene ring despite the rate-accelerating association through hydrogen bounding. Moreover, the validity of the proposed mechanistic concept of hydrogen bonding is substantiated in the reactivity trends observed for several α-oxygen-substituted substrates (Table 2). Thus, inspection of the data makes evident that the methoxy and acetoxy derivatives react more slowly than the naphthyl alcohols, as expected on account of their lack of hydrogen bonding; consequently, the more reactive substrates are also the more diastereoselective ones. Similar trends are documented in the stereoselective Schenck ene reaction (ref 35), Finally, the acylation of allylic alcohols may quite generally even completely suppress their reaction with singlet oxygen (ref 17a), which is in line with the proposed attractive interaction through hydrogen bonding.
136. Prein, M.; Adam, W.; Maurer, M.; Peters, E. M.; Peters, K.; von Schnering, H. Chem. Eur. J. 1995, 1, 89-94.
137. Frimer, A. A.; Stephenson, L. M. In Singlet Oxygen; Frimer, A. A., Ed.; CRC Press: Boca Raton, FL, 1985; Vol. 2, p 67.
138. The reported trapping experiments do not necessarily prove the intermediacy of perepoxides in the ene reaction since substrates have been employed which do not undergo ene reactions (e.g., Schaap, A. P.; Recher, S. C.; Faler, G. R.; Villasenor, S. R. J. Am. Chem. Soc. 1983, 705, 1691-1693); moreover, also open-chain zwitterions or exciplexes (ref 21c) may be trapped to form identical products (cf. Jefford, C. W Chem. Soc. Rev. 1993, 59-66).
139. The reported trapping experiments do not necessarily prove the intermediacy of perepoxides in the ene reaction since substrates have been employed which do not undergo ene reactions (e.g., Schaap, A. P.; Recher, S. C.; Faler, G. R.; Villasenor, S. R. J. Am. Chem. Soc. 1983, 705, 1691-1693); moreover, also open-chain zwitterions or exciplexes (ref 21c) may be trapped to form identical products (cf. Jefford, C. W Chem. Soc. Rev. 1993, 59-66).
140. A diminished directing effect of the hydroxy group in cyclic systems was also observed in the singlet oxygen ene reaction; cf. ref 35c.
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146. The different extent of charge transfer also provides a satisfactory rationale for the solvent effects in the photooxygenation of chiral olefins and dienes. Polar solvents promote charge transfer (cf refs 28 and 29), and consequently, stabilization of the exciplex by intramolecular hydrogen bonding with the hydroxy group is ineffective and loss of stereocontrol is expected and observed.