Synthesis of α-Prolinols and 2-Amino-1,5-diols from Primary Nitroalkanes and Other Simple Precursors via Intermediacy of 5,6-Dihydro-4H-1,2-oxazines

Synthesis of α-Prolinols and 2-Amino-1,5-diols from Primary Nitroalkanes and Other Simple Precursors via Intermediacy of 5,6-Dihydro-4H-1,2-oxazines Full article

Journal

Synthesis-Stuttgart
ISSN: 1437-210X , E-ISSN: 0039-7881

Output data

Year: 2012, Volume: 44, Number: 12, Pages: 1898-1906 Pages count : 9 DOI: 10.1055/s-0031-1290973

Authors

Tabolin Andrey ¹ , Ioffe Sema ¹ , Lesiv Alexey ¹ , Khomutova Yulia ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences

A new strategy for the synthesis of 2-(1-hydroxyalkyl)pyrrolidines and 2-amino-1,5-diols is suggested. The target compounds can be obtained in high yields from available precursors through the intermediacy of six-membered cyclic nitronates and their rearrangement products. Successive reduction of the latter led to the target products with moderate to high diastereoselectivity.

Tabolin A. , Ioffe S. , Lesiv A. , Khomutova Y.
Synthesis of α-Prolinols and 2-Amino-1,5-diols from Primary Nitroalkanes and Other Simple Precursors via Intermediacy of 5,6-Dihydro-4H-1,2-oxazines
Synthesis-Stuttgart. 2012. V.44. N12. P.1898-1906. DOI: 10.1055/s-0031-1290973 WOS Scopus OpenAlex

≡ Web of science:	WOS:000305391500016
≡ Scopus:	2-s2.0-84861897326
≡ OpenAlex:	W2315739040

Synthesis of α-Prolinols and 2-Amino-1,5-diols from Primary Nitroalkanes and Other Simple Precursors via Intermediacy of 5,6-Dihydro-4H-1,2-oxa­zines Full article

Synthesis of α-Prolinols and 2-Amino-1,5-diols from Primary Nitroalkanes and Other Simple Precursors via Intermediacy of 5,6-Dihydro-4H-1,2-oxazines Full article