Categories: C-C Bond Formation > Nitrogen-containing molecules >
Synthesis of 1,2-amino alcohols
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Recent Literature
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.
The photoredox-catalyzed reaction of TMSCH2OPMP with imines provides β-amino ethers
or β-amino alcohols in a
sequential one-pot protocol under high-efficiency, mild, and metal or
metal-free conditions. TMSCH2OPMP serves as a synthetic equivalent of α-hydroxymethyl radical
and enables an optional in situ photocatalyzed oxidative PMP
group deprotection strategy under air.
A. Gontala, H. Huh, S. K. Woo, Org. Lett., 2023, 25,
21-26.
In the presence of a chiral oxazaborolidinium ion catalyst and a
photosensitizer, an enantioselective visible light mediated addition of an
α-aminoalkyl radical to aryl methyl ketones provides chiral 1,2-amino tertiary
alcohol derivatives in high yields with excellent enantioselectivities.
S. M. Cho, J. Y. Kim, S. Han, D. H. Run, J. Org. Chem., 2022, 87,
11196-11203.
A Cr-catalyzed asymmetric cross aza-pinacol coupling of aldehydes and N-sulfonyl
imines provides β-amino alcohols bearing vicinal stereocenters. This protocol
proceeds in a radical-polar crossover manner from the intermediacy of an α-amino
radical instead of a ketyl radical.
H. Hu, Z. Wang, J. Am. Chem. Soc.,
2023, 145, 20775-20781.
An electrochemical method enables the direct synthesis of β-amino alcohols
via a reductive cross coupling of imines with ketones at the cathode involving
radicals. The use of abundant and easily prepared starting materials, high atom-
and step-economy, and insensitivity to air and moisture make this synthetic
strategy very efficient.
W.-M. Zeng, W.-F. Dong, Y.-H. He, Y.-N. Zhao, Z. Guan, J. Org. Chem., 2023, 88,
1625-1634.
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.