Stereoselective Yang cyclizations of α-amido ketones
(Note: The full text of this document is currently only available in the PDF Version )
Axel G. Griesbeck, Heike Heckroth and Johann Lex
Abstract
The photocyclization of methyl-substituted α-acetamido butyrophenone derivatives is highly stereoselective and leads to 2-aminocyclobutanols with complete control of three new stereogenic centers.
References
N. C. Yang and D.-D. H. Yang, J. Am. Chem. Soc., 1958, 80, 2913 CrossRefCAS.
J. C. Scaiano, Acc. Chem. Res., 1982, 15, 252 CrossRefCAS; L. J. Johnston and J. C. Scaiano, Chem. Rev., 1989, 89, 521 CrossRefCAS.
A. E. Dorigo, M. A. McCarrick, R. J. Loncharich and K. N. Houk, J. Am. Chem. Soc., 1990, 112, 7508 CrossRefCAS; R. R. Sauers and L. A. Edberg, J. Org. Chem., 1994, 59, 7061 CrossRefCAS.
P. J. Wagner and B.-S. Park, Org. Photochem., 1991, 11, 227 Search PubMed; P. J. Wagner,
in Handbook of Photochemistry and Photobiology,
ed. W. M. Horspool and P.-S. Song,
CRC Press,
Boca Raton,
1995,
p. 449 Search PubMed.
A. G. Griesbeck, Chimia, 1998, 52, 272 CAS; A. G. Griesbeck, EPA Newsl., 1998, 3 Search PubMed; A. G. Griesbeck, Liebigs Ann. Chem., 1996, 1951 Search PubMed.
O. Itoh, T. Honnami, A. Amano, K. Murata, Y. Koichi and T. Sugita, J. Org. Chem., 1992, 57, 7334 CrossRefCAS.
Quantum yields by actinometry (GC product analyses) using valerophenone
as standard with ΦF= 0.33: P. J. Wagner and A. E. Kemppainen, J. Am. Chem. Soc., 1972, 94, 7495 Search PubMed.
F. D. Lewis and T. A. Hilliard, J. Am. Chem. Soc., 1972, 94, 3852 CrossRefCAS.
T. Hasegawa, Y. Arata, M. Endoh and M. Yoshioka, Tetrahedron, 1985, 41, 1667 CrossRefCAS; T. Hasegawa, Y. Arata and A. Kageyama, Tetrahedron Lett., 1983, 24, 1995 CrossRefCAS.
M. Klessinger, Pure Appl. Chem., 1997, 69, 773 CrossRefCAS.
A. G. Griesbeck, S. Stadtmüller and H. Mauder, Acc. Chem. Res., 1994, 27, 70 CrossRefCAS.