By M. Harmata
The improvement and alertness of cycloaddition technique remains to be on the leading edge of study in man made natural chemistry. This quantity starts with a evaluation of tools to be had for the synthesis of 7-membered earrings and is with paintings on metal-catalyzed cycloadditions. there's then an replace at the cycloaddition chemistry of 2-pyrone, after which a different software of photocycloaddition is exact. the ultimate bankruptcy is a dialogue of the newest explorations of the response of rhodium-stabilized vinyl carbenoids with dienes.
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Extra resources for Advances in Cycloaddition. Volume 5
I. INTRODUCTION Because of the aromatic character of 2-pyrones, they enter into [4+2] cycloadditions less readily than most cyclic conjugated dienes. Nevertheless, the ability of these heteroaromatic compounds to act as dienes in [4+2] cycloadditions was reported by Diels and Alder only three years after they first reported the [4+2] cycloaddition between dienes and dienophiles which bears their names. 1 In the decades following the first report of 2-pyrones acting as dienes, this methodology was occasionally employed by synthetic chemists, but up until the early 1970s the use of this methodology was largely confined to synthesizing aromatic products (1 and 4).
Lankford, P. ; Miller, R. ; Murray, C. ; Yang, D. C. J. Am. Chem. Soc. 1990, 112, 3642. 38. Davies, H. M. ; Matasi, J. ; Hodges, L. ; Huby, N. J. ; Houser, J. H. J. Org. Chem. 1997, 62, 1095. 39. Griesbeck, A. G. J. Prakt. Chem. 1993, 335, 489. 40. Wender, P. ; Eissenstat, M. ; Filosa, M. P. J. Am. Chem. Soc. 1979, 101, 2196. 41. Davies, H. M. ; Doan, B. D. J. Org. Chem. 1998, 63, 657. For additional examples of the scope of this reaction, see Davies, H. M. ; Matasi, J. ; Hodges, L. ; Huby, N.
50 52 52 54 54 56 80 80 80 Advances in Cycloaddition Volume 5, pages 47-83. Copyright 9 1999 by JAI Press Inc. All rights of reproduction in any form reserved. ISBN: 0-7623-0346-8 47 48 BENJAMIN T. WOODARD and GARY H. POSNER ABSTRACT This review of recent progress in [4+2] cycloaddition of 2-pyrone dienes emphasizes control of relative and absolute stereochemistry. Discussion includes the development of mild reaction conditions and electronic matching of reaction partners, allowing the isolation of bicyclic lactones with control of relative stereochemistry.