Harvesting the strain installed by a Paternò-Büchi step in a synthetically useful way: high-yielding photoprotolytic oxametathesis in polycyclic systems.
نویسندگان
چکیده
High-yielding one-pot photoinduced transformation of readily available endoaroyl and heteroaroyl Diels-Alder adducts into novel polycyclic aldehydes or their hemiacetals, decorated by carbo- and heterocyclic pendants, is described.
منابع مشابه
Photoinduced intramolecular cyclopentanation vs photoprotolytic oxametathesis in polycyclic alkenes outfitted with conformationally constrained aroylmethyl chromophores.
Intramolecular photoinduced cyclizations are investigated in photoprecursors assembled in a modular fashion via a Diels-Alder reaction of acetylenic dienophiles with subsequent Michael additions of aromatic ketones to install a chromophore capable of initiating Paternò-Büchi cycloadditions or radical cyclization cascades. The protolytic oxametathesis in these systems allows for rapid access to ...
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Chromones are introduced into a double-tandem [4(π)+2(π)]·[2(π)+2(π)]·[4(π)+2(π)]·[2(π)+2(π)] synthetic sequence, culminating in photoprotolytic oxametathesis, which leads to an expeditious growth of molecular complexity over a few experimentally simple steps. The overall reaction can potentially be utilized in diversity-oriented synthesis, as it allows for three or more diversity inputs furnis...
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عنوان ژورنال:
- Organic letters
دوره 11 17 شماره
صفحات -
تاریخ انتشار 2009