TY - JOUR
T1 - 1-Naphthylmethyl and 1-naphthylmethoxymethyl protecting groups
T2 - New members of the benzyl- and benzyloxymethyl-type family
AU - Sato, Takuya
AU - Joh, Yohei
AU - Oishi, Tohru
AU - Torikai, Kohei
N1 - Funding Information:
We are grateful to Profs. Ken Sakai and Kosei Yamauchi (Kyushu University) for providing us with access to cyclic voltammetry instrumentation, and to Prof. Masahiko Suenaga (Kyushu University) for invaluable discussions. We also thank Mr. Keiya Yamamoto (Kyushu University) for technical support with cyclic voltammetry measurements. Mr. Naoto Yanai (our laboratory) is acknowledged for providing 6a. This work was financially supported by a Grant-in-Aid for Young Scientists (B) (No. 15K21210 to K.T.) from the JSPS – Japan, and a grant from Wako Pure Chemical Industries (to K.T.), as well as by a Wako Award in Synthetic Organic Chemistry (Japan). K.T. would like to express his deepest gratitude to Ms. Miyoko Ueno, Mr. and Ms. Takaaki and Rumiko Torikai, Mr. Kazuo Fushiki, Ms. Yukiko Ueno, and Mr. and Ms. Motoaki and Michie Yamaoka for their generous financial donations to his project. The authors declare that a patent regarding the use of NAPOMCl for the protection of alcohols and thiols is pending (PCT Int. Appl. WO 2016056448 A1 20160414, 2016).
Publisher Copyright:
© 2017 Elsevier Ltd
PY - 2017
Y1 - 2017
N2 - 1-Naphthylmethyl (NAPI) and 1-naphthylmethoxymethyl (NAPOMI) protecting groups were developed as new members of the benzyl- and benzyloxymethyl-type family. NAPI and NAPOMI can be introduced under conventional conditions, such as NAPIBr/NaH/room temperature (rt), or NAPOMICl/i-Pr2EtN/rt. They can also be removed under conventional conditions, e.g., by dichlorodicyanobenzoquinone (DDQ)- or ceric ammonium nitrate (CAN)-mediated oxidation, or by hydrogenolysis. The specific advantages of these new protecting groups are: i) a less costly synthesis of NAPOMICl compared to NAPOMIICl, ii) the possibility to remove NAPOMII selectively in the presence of NAPOMI by DDQ-mediated oxidation, and iii) the compatibility with strong acids even in the presence of hard nucleophiles.
AB - 1-Naphthylmethyl (NAPI) and 1-naphthylmethoxymethyl (NAPOMI) protecting groups were developed as new members of the benzyl- and benzyloxymethyl-type family. NAPI and NAPOMI can be introduced under conventional conditions, such as NAPIBr/NaH/room temperature (rt), or NAPOMICl/i-Pr2EtN/rt. They can also be removed under conventional conditions, e.g., by dichlorodicyanobenzoquinone (DDQ)- or ceric ammonium nitrate (CAN)-mediated oxidation, or by hydrogenolysis. The specific advantages of these new protecting groups are: i) a less costly synthesis of NAPOMICl compared to NAPOMIICl, ii) the possibility to remove NAPOMII selectively in the presence of NAPOMI by DDQ-mediated oxidation, and iii) the compatibility with strong acids even in the presence of hard nucleophiles.
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U2 - 10.1016/j.tetlet.2017.04.046
DO - 10.1016/j.tetlet.2017.04.046
M3 - Article
AN - SCOPUS:85018989380
SN - 0040-4039
VL - 58
SP - 2178
EP - 2181
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 23
ER -