Mannich-Type Reaction of Aldimines with 2-Silyloxydienes Catalyzed by Ammonium Chloride - International Journal of Organic Chemistry

IJOC > Vol.9 No.4, December 2019

International Journal of Organic Chemistry

Volume 9, Issue 4 (December 2019)

ISSN Print: 2161-4687 ISSN Online: 2161-4695

Google-based Impact Factor: 1.15 Citations

Mannich-Type Reaction of Aldimines with 2-Silyloxydienes Catalyzed by Ammonium Chloride ()

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DOI: 10.4236/ijoc.2019.94014 817 Downloads 1,924 Views Citations

Author(s)

Shoichi Fukumoto, Miho Shigenobu, Kaori Ishimaru

Affiliation(s)

Department of Applied Chemistry, National Defence Academy, Hashirimizu, Yokosuka, Japan.

ABSTRACT

Reaction of imines with 2-silyloxydiene catalyzed by ammonium chloride has been perfectly proceeded under environmentally friendly conditions to give Mannich-type product selectively. The reaction would proceed via Mannich-type mechanism, not cyclization/ring-opening process. Cyclopropanation of the corresponding Mannich-type product gave the precursor of prasugrel skeleton in high yield.

KEYWORDS

Mannich-Type Reaction, Ammonium Chloride, Imine, 2-Silyloxydiene

Share and Cite:

Fukumoto, S. , Shigenobu, M. and Ishimaru, K. (2019) Mannich-Type Reaction of Aldimines with 2-Silyloxydienes Catalyzed by Ammonium Chloride. International Journal of Organic Chemistry, 9, 163-173. doi: 10.4236/ijoc.2019.94014.

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