An Acid-Stabletert-Butyldiarylsilyl (TBDAS) Linker for Solid-Phase Organic Synthesis

Abstract

[reaction: see text] A new, robust tert-butyldiarylsilyl (TBDAS) linker has been developed for solid-phase organic synthesis. This linker is stable to both protic and Lewis acidic reaction conditions, overcoming a significant limitation of previously reported silyl linkers. Solid-phase acetal deprotection, olefination, asymmetric allylation, and silyl protecting group deblocking reactions have been demonstrated with TBDAS-linked substrates.

Aerobic Oxidative Amidation of Aromatic and Cinnamic Aldehydes with Secondary Amines by CuI/2-Pyridonate Catalytic System

“…1 1-(4-Phenylbenzoyl)piperidine (3b). 25 Purification was performed by column chromatography on silica gel eluting with EtOAc/ Hexane = 1:1 to give 3b as a pale yellow solid, 178.4 mg, 67% yield. 1-(4-Methoxybenzoyl)piperidine (3c).…”

Synthesis of the Sex Pheromone of the Tea Tussock Moth Based on a Resource Chemistry Strategy

“…[17] [α] D 20 + 10.4 ( c 0.7, CHCl 3 ). Next, at −78–−50 °C, a Julia-Kocienski reaction was performed between 5-(isobutylsulfonyl)-1-phenyl-1 H -tetrazole ( 8 ), which was prepared according to the literature [21] and the chiral aldehyde 7 , affording the coupling product 9 in 87% yield ( E/Z ratio of 1:1). The subsequent hydrogenation of the C=C double bond and removal of the benzyl protecting group was achieved in one-pot in 86% yield.…”

Asymmetric Synthesis on Solid Support

“…Tan and coworkers 16 reported the asymmetric allylation of an aliphatic polymer-supported aldehyde using a strained allylsilacycle 24 developed by Leighton and coworkers 17 (Scheme 7.4b). The homoallylic alcohol 25 was obtained in good enantiopurity and yields.…”