Dearomative Alkylation-Based Two-Step cis-Diastereoselective Synthesis of Indoline-2,3-Fused Chromans and Tetrahydropyrans
Raju Chouhan,
Nandini Ray,
Nitish Nayan Gogoi
et al.
Abstract:Herein, we describe a two-step, cis-diastereoselective
synthesis of indoline-2,3-fused chromans from 3-substituted indoles.
The method proceeds without intermediacy of ortho-quinone methides and leverages the dual function of TBS-protected
2-hydroxybenzyl iodides both as highly reactive alkylating agents
in a t-BuONa/Et3B-promoted dearomative
alkylation step and as a source of masked phenoxide nucleophiles in
a subsequent TBAF-induced one-pot deprotection-cyclization step of
the resulting indolenines. Importan… Show more
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