Intramolecular Diels–Alder Reactions
1991; Elsevier BV; Linguagem: Inglês
10.1016/b978-0-08-052349-1.00131-1
Autores Tópico(s)Synthetic Organic Chemistry Methods
ResumoThe Diels–Alder reaction, first described in 1928,1 has enjoyed widespread use in organic synthesis.2 This [4 + 2] cycloaddition is particularly valuable in that it forms two bonds in a cyclohexenyl system with simultaneous creation of up to four new stereocenters. Curiously, the intramolecular version in which the diene and dienophile are tethered by a connecting chain was not investigated for many years. Alder and Schumaker reported the first example of the intramolecular reaction in 1953,3 but it was not until the early 1960s that additional examples began to appear in the literature.4 Since the mid-1970s, however, a virtual explosion of interest in this reaction has occurred.5 The increased reactivity (due to favorable entropy considerations) and heightened regioselectivity (due to constraints posed by the connecting chain), as well as the potential for the synthesis of stereochemically complex polycyclic ring systems, account for the growth of applications of this reaction in organic and particularly natural products synthesis.
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