Qiwei Lang, Gen-Qiang Chen and Xumu Zhang of the Southern University of
Science and Technology achieved high ee in the reduction of the readily
available lactol 1 to the lactone 2
(Chem. Price of N-Methyltetrahydro-2H-pyran-4-amine Sci. Fmoc-Lys(Me)2-OH (hydrochloride) Chemscene 2023, 14, 4888.
DOI: 10.1039/D3SC00491K).
Bi-Jie Li of Tsinghua University also observed high ee in the reduction of the enamide
3 to the α-silyl amide 4
(Angew. Chem. Int. PMID:24516446 Ed. 2023, 62, e202214534.
DOI: 10.1002/anie.202214534).
Liang Yin of the Shanghai Institute of Organic Chemistry showed that the conjugate addition
of phenylselenol to the thioamide 5 delivered the selenide 6 in high ee
(Angew. Chem. Int. Ed. 2023, 62, e202301422.
DOI: 10.1002/anie.202301422).
Zhongxing Huang of the University of Hong
Kong reduced the malonate 7 to the monoester 8
(Org. Chem. Front. 2023, 10, 1675.
DOI: 10.1039/D2QO02055F).
Wei Shu, also of the Southern University of Science and Technology, assembled
the amide 11 by coupling the bromide 10 with the α-bromo amide 9
(Nature Commun. 2023, 14, 2938.
DOI: 10.1038/s41467-023-38702-3).
Ken Yamazaki of Okayama University and Darren J. Dixon of the
University of Oxford used a bifunctional iminophosphorane superbase to mediate
the addition of nitromethane to ethyl sorbate 12, leading to 13
(Angew. Chem. Int. Ed. 2023, 62, e202303391.
DOI: 10.1002/anie.202303391).
Changkun Li of Shanghai Jiao Tong University
showed that Rh-catalyzed coupling of the secondary allylic carbonate 14
with
acetonitrile led to 15 with high regioselectivity
(J. Am. Chem. Soc. 2023, 145, 3897.
DOI: 10.1021/jacs.3c00244).
Martin Oestreich of the Technische Universität Berlin constructed the
alkenyl germane 18 (readily convertible to the corresponding alkenyl halide)
by coupling the organozinc 17 with the α-bromo germane 16
(Org. Lett. 2023, 25, 1901.
DOI: 10.1021/acs.orglett.3c00410).
Taichi Kano of the Tokyo University of Agriculture and Technology showed
that the alkenyl boronic acid 20 added to the enone 19 with high
regioselectivity, leading to 21
(Org. Lett. 2023, 25, 1497.
DOI: 10.1021/acs.orglett.3c00262).
Jesús M. Garcia of the Universidad Pública de Navarra and Mikel Oiarbide and Claudio Palomo of the
Universidad del Pais Basco established the α-hydroxy enone 22 as a useful
surrogate for acrylate and acrolein in the Hayashi-Jørgensen catalyzed
conjugate
addition of the aldehyde 23
(Org. Biomol. Chem. 2023, 21, 4833.
DOI: 10.1039/D3OB00475A).
Ken-ichi Yamada of Tokushima University optimized the N-heterocyclic carbene
catalyst for the Stetter cyclization of the aldehyde 25 to the ketone 26
(Chem. Commun. 2023, 59, 5375.
DOI: 10.1039/D3CC00693J).
Simon J. Meek of the University of North Carolina used
the mixed anhydride 28 to acylate the bis-boronate 27, leading to the ketone
29
(Angew. Chem. Int. Ed. 2023, 62, e202215855.
DOI: 10.1002/anie.202215855).
Enterolactone (33) is formed by the action of intestinal bacteria on plant
lignan precursors present in the diet. Uttam K. Tambar of the University of
Texas Southwest Medical Center assembled 32 by the MacMillan amine catalyst
A-catalyzed alkylation of the aldehyde 31 with the pyridinium salt 30, followed
by reduction. The initial mixture of diastereomers was equilibrated to the more stable 33
(Chem. Sci. 2023, 14, 586.
DOI: 10.1039/D2SC05654B).
