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Chemoselective reductions of 2‐acyl‐1 H ‐indole‐3‐carboxaldehydes
Author(s) -
Djurić Stevan W.,
Herbert Richard B.,
Holliman Frederick G.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220561
Subject(s) - chemistry , sodium cyanoborohydride , indole test , yield (engineering) , hydroxymethyl , acetic acid , organic chemistry , combinatorial chemistry , metallurgy , materials science
A novel procedure for the chemoselective reduction of 2‐acyl‐1 H ‐indole‐3‐carboxaldehydes has been developed. Low temperature lithium triethylborohydride reduction affords the indol‐2‐yl carbinol whilst sodium cyanoborohydride reduction in acetic acid affords the 3‐hydroxymethyl analogs. Both processes are high yield, and provide access to intermediates of potential utility for indole alkaloid synthesis.