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Synthesis of 1,2-amino alcohols

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A Cr/photoredox dual catalytic system enables the synthesis of protected 1,2-amino alcohols starting from carbonyl compounds and α-silyl amines via in situ generation of α-amino carbanion equivalents which act as nucleophiles. The unique nature of this reaction was demonstrated through the aminoalkylation of ketones and an acyl silane.
J. L. Schwarz, R. Kleinmans, T. O. Paulisch, F. Glorius, J. Am. Chem. Soc., 2020, 142, 2168-2174.


Acyloxymethyl radicals, that add to imines, were generated from the corresponding iodomethyl esters by the action of dimethylzinc or triethylborane. A facile hydrolysis of the acyloxy moiety of the adducts gave the corresponding amino alcohols in good yield.
K.-i. Yamada, M. Nakano, M. Maekawa, T. Akindele, K. Tomioka, Org. Lett., 2008, 10, 3805-3808.


Phthalimido-allene and primary alcohols engage in an iridium-catalyzed enantioselective hydrogen auto-transfer-mediated carbonyl reductive coupling to provide vicinal amino alcohols with high levels of regio-, anti-diastereo-, and enantioselectivity.
K. Spielmann, M. Xiang, L. A. Schwartz, M. J. Krische, J. Am. Chem. Soc., 2019, 141, 14136-14141.


N-Benzyldiphenylphosphinamides are deprotonated at the NCα position diastereospecifically upon treatment with t-BuLi in diethyl ether at low temperature. Reaction of the anions with various electrophiles and subsequent cleavage of the P-N linkage affords 1,2-amino alcohols and α-, β-, and γ-amino acids.
P. O. Burgos, I. Fernández, M. J. Iglesias, S. García-Granda, F. L. Ortiz, Org. Lett., 2008, 10, 537-540.


A highly efficient, mild and practical approach for the synthesis of optically pure β-amino alcohols by the SmI2-induced reductive cross-coupling of various chiral N-tert-butanesulfinyl imines with aldehydes was developed.
Y.-W. Zhong, Y.-Z. Dong, K. Fang, K. Izumi, M.-H. Xu, G.-Q. Lin, J. Am. Chem. Soc., 2005, 127, 11956-11957.