68754-15-4Relevant articles and documents
Dynamic Kinetic Resolution of Allylic Azides via Asymmetric Dihydroxylation
Ott, Amy A.,Goshey, Charles S.,Topczewski, Joseph J.
supporting information, p. 7737 - 7740 (2017/06/21)
The catalytic enantioselective preparation of densely functionalized amines is a fundamental synthetic challenge. To address this challenge, we report for the first time that the Winstein rearrangement can be enlisted as the racemization pathway in a dynamic kinetic resolution of allylic azides. Alkene functionalization by Sharpless dihydroxylation affords tertiary azides in excellent enantioselectivity (up to 99:1 er). This approach establishes the chirality of the tertiary azide, obviates the need to directly forge either a congested C-N or C-C bond at the new nitrogenous stereocenter, and establishes additional functionality. Several examples demonstrate further elaboration of this functionality.
Electrochemical Synthesis of Sobrerol O-Derivatives
Gora, J.,Smigielski, K.,Kula, J.
, p. 759 - 761 (2007/10/02)
(+/-)-α-Pinene (1) has been converted electrochemically to (+/-)-cis/trans-sobrerol dimethyl ether (2a/2b) and (+/-)-trans-sobrerol diacetate (3), which can be hydrolyzed to (+/-)-trans-sobrerol (5) or its monoacetate (4).
