Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 18, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202114118
Keywords
Chain-Length Selectivity; Chemoselectivity; Molecular Recognition; Organocatalysis; Silylation
Categories
Funding
- Kobayashi Foundation
- Uehara Memorial Foundation
- Sasakawa Scientific Research Grants
- [JP21H02604]
- [JP20K06964]
- [JP21H05078]
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Catalyst-controlled substrate-selective silylation of alcohols is achieved independently of the reactivity of hydroxy group based on steric environment. The reaction shows high selectivity towards 1,5-amino alcohol derivatives and discriminating ability towards remote functionality at C(5) from reacting hydroxy groups in the silylation of pentanol analogues.
Silylation of alcohols has generally been known to take place at the sterically most accessible less-hindered hydroxy group. Herein, the catalyst-controlled substrate-selective silylation of primary alcohols, in which the selectivity was controlled independently of the innate reactivity of the hydroxy group, based on the steric environment, is reported. The chain-length-selective silylation of 1,n-amino alcohol derivatives was achieved and 1,5-amino alcohol derivatives showed outstandingly high reactivity in the presence of analogues with a shorter or longer chain length under catalyst-controlled conditions. A highly substrate-selective catalytic silylation of pentanol analogues was also developed, in which the remote functionality at C(5) from the reacting hydroxy groups was effectively discriminated on silylation.
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