title: SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes.
abstract: Interest in saturated N-heterocycles as scaffolds for the synthesis of bioactive molecules is increasing. Reliable and predictable synthetic methods for the preparation of these compounds, especially medium-sized rings, are limited. We describe the development of SnAP (Sn amino protocol) reagents for the transformation of aldehydes into seven-, eight- and nine-membered saturated N-heterocycles. This process occurs under mild, room-temperature conditions and offers exceptional substrate scope and functional-group tolerance. Air- and moisture-stable SnAP reagents are prepared on a multigram scale from inexpensive starting materials by simple reaction sequences. These new reagents and processes allow widely available aryl, heteroaryl and aliphatic aldehydes to be converted into diverse N-heterocycles, including diazepanes, oxazepanes, diazocanes, oxazocanes and hexahydrobenzoxazonines, by a single synthetic operation.
authors.affiliation: 1] Laboratorium für Organische Chemie, ETH-Zürich, Wolfgang Pauli Strasse 10, Zürich 8093, Switzerland. [2].
authors.forename: Cam-Van T
authors.initials: CV
authors.lastname: Vo
authors.affiliation: 1] Laboratorium für Organische Chemie, ETH-Zürich, Wolfgang Pauli Strasse 10, Zürich 8093, Switzerland. [2].
authors.forename: Michael U
authors.initials: MU
authors.lastname: Luescher
authors.affiliation: Laboratorium für Organische Chemie, ETH-Zürich, Wolfgang Pauli Strasse 10, Zürich 8093, Switzerland.
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode