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  • SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes.

SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes.

Nature chemistry (2014-03-22)
Cam-Van T Vo, Michael U Luescher, Jeffrey W Bode
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
SnAP Pip Reagent
Sigma-Aldrich
SnAP OA Reagent
Sigma-Aldrich
SnAP DA Reagent
Sigma-Aldrich
SnAP TM Reagent
Sigma-Aldrich
SnAP 3-Spiro-(4-Pip) M Reagent
Sigma-Aldrich
SnAP 3Me-M Reagent
Sigma-Aldrich
SnAP M Reagent, 95%