TY - JOUR
T1 - Sequential Norrish-Yang Cyclization and C-C Cleavage/Cross-Coupling of a [4.1.0] Fused Saturated Azacycle
AU - Roberts, Charis Amber
AU - Park, Bohyun
AU - Xu, Li Ping
AU - Roque, Jose B.
AU - Yeung, Charles S.
AU - Musaev, Djamaladdin G.
AU - Sarpong, Richmond
AU - Lalonde, Rebecca Lyn
N1 - Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/9/3
Y1 - 2021/9/3
N2 - Methods that functionalize the periphery of azacylic scaffolds have garnered increasing interest in recent years. Herein, we investigate the selectivity of a solid-state Norrish-Yang cyclization (NYC) and subsequent C-C cleavage/cross-coupling reaction of a strained cyclopropane-fused azacyclic system. Surprisingly, the NYC primarily furnished a single lactam constitutional and diastereo-isomer. The regioselectivity of the C-C cleavage of the α-hydroxy-β-lactam moiety could be varied by altering the ligand set used in the coupling chemistry. Experimental and computational observations are discussed.
AB - Methods that functionalize the periphery of azacylic scaffolds have garnered increasing interest in recent years. Herein, we investigate the selectivity of a solid-state Norrish-Yang cyclization (NYC) and subsequent C-C cleavage/cross-coupling reaction of a strained cyclopropane-fused azacyclic system. Surprisingly, the NYC primarily furnished a single lactam constitutional and diastereo-isomer. The regioselectivity of the C-C cleavage of the α-hydroxy-β-lactam moiety could be varied by altering the ligand set used in the coupling chemistry. Experimental and computational observations are discussed.
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U2 - 10.1021/acs.joc.1c01466
DO - 10.1021/acs.joc.1c01466
M3 - Article
C2 - 34399579
AN - SCOPUS:85114139912
SN - 0022-3263
VL - 86
SP - 12436
EP - 12442
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 17
ER -