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. Author manuscript; available in PMC: 2013 May 7.
Published in final edited form as: Chemistry. 2012 Mar 30;18(19):5826–5831. doi: 10.1002/chem.201200629

Scheme 4.

Scheme 4

Synthesis of the pyrrolo[1,2-a]azepine core 2. a) (R)-tert-butyl sulfinamide, Ti(OEt)4, CH2Cl2, 95%; b) (2(-1,3-dioxan-2-yl)ethyl)magnesium bromide, THF, −45 °C, 88% (>9:1 dr); c) LiHMDS, allyl bromide, DMF, −20 °C to rt, 80%; d) Grubbs II (5 mol%), CH2Cl2, 40 °C, 1 h, 78%; e) H2, Pd/C; f) i) TFA:H20 (95:5), rt, 5 min; ii) PS- BH(OAc)3, 86% for two steps.