Ortho-TMS benzaldehyde, an effective bifunctional linchpin for Type II Anion Relay Chemistry (ARC), permits efficient multi-component union of a variety of nucleophiles and electrophiles, including the first example of a Pd-mediated ARC Type II process. To demonstrate the utility of the Type II ARC protocol, a “proof of concept” synthetic sequence was designed and implemented for construction of a focused library of “natural product-like” compounds.
Palladium/ClickFerrophos-Catalyzed Asymmetric Domino Allylstannylation–Heck Reaction of <i>o</i>-Formylaryl Triflate
作者:Atsuo Tada、Yuichiro Tokoro、Shin-ichi Fukuzawa
DOI:10.1021/jo5010247
日期:2014.9.5
Asymmetric domino allylstannylation-Heck reaction of o-formylaryl triflates was successively catalyzed by Pd/ClickFerrophos to give the 3-methylene-indan-1-ols in good yields with good to excellent enantioselectivities. The benefit of the reaction is that the starting o-formylaryl triflates are prepared from easily accessible salicylaldehyde derivatives, and the variation of the product, chiral 3-methylene-indan-1-ols, can be expanded. The reaction with 4-substituted substrates gave the corresponding 3-methylene-indan-1-ols in good yields with high enantioselectivities, whereas the reaction with 5- and 6-substituted substrates occasionally afforded the corresponding Stille coupling product in significant amounts along with the desired 3-methylene-indan-1-ols.
<i>Ortho</i>-TMS Benzaldehyde: An Effective Linchpin for Type II Anion Relay Chemistry (ARC)
作者:Amos B. Smith、Won-Suk Kim、William M. Wuest
DOI:10.1002/anie.200802301
日期:2008.9.1
Ortho-TMS benzaldehyde, an effective bifunctional linchpin for Type II Anion Relay Chemistry (ARC), permits efficient multi-component union of a variety of nucleophiles and electrophiles, including the first example of a Pd-mediated ARC Type II process. To demonstrate the utility of the Type II ARC protocol, a “proof of concept” synthetic sequence was designed and implemented for construction of a focused library of “natural product-like” compounds.