TY - JOUR
T1 - 2-Nitro-cyclopropyl-1-carbonyl Compounds from Unsaturated Carbonyl Compounds and Nitromethane via Enolonium Species
AU - Ghosh, Asit
AU - Lipisa, Yuriy B.
AU - Fridman, Natalia
AU - Szpilman, Alex M.
N1 - Publisher Copyright:
© 2023 American Chemical Society.
PY - 2023/2/17
Y1 - 2023/2/17
N2 - 2-Nitrocyclopropanes bearing ketones, amides, esters, and carboxylic acids in the 1 position may be accessed as single diastereoisomers in one operation from the corresponding unsaturated carbonyl compounds. The source of the nitro-methylene component is nitromethane. The reaction proceeds at room temperature under mild conditions. The products may be converted into, e.g., cyclopropyl-amino acids in a single step. Both nitrocyclopropanes and amino-cyclopropanes are unique moieties found in biologically active compounds and natural products.
AB - 2-Nitrocyclopropanes bearing ketones, amides, esters, and carboxylic acids in the 1 position may be accessed as single diastereoisomers in one operation from the corresponding unsaturated carbonyl compounds. The source of the nitro-methylene component is nitromethane. The reaction proceeds at room temperature under mild conditions. The products may be converted into, e.g., cyclopropyl-amino acids in a single step. Both nitrocyclopropanes and amino-cyclopropanes are unique moieties found in biologically active compounds and natural products.
UR - http://www.scopus.com/inward/record.url?scp=85147963937&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.2c02125
DO - 10.1021/acs.joc.2c02125
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AN - SCOPUS:85147963937
SN - 0022-3263
VL - 88
SP - 1977
EP - 1987
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -