TY - JOUR

T1 - Transition Metal-Catalyzed Synthesis of 3-Coumaranone-Containing NH-Aziridines from 2H-Azirines

T2 - Nickel(II) versus Gold(I)

AU - Sakharov, Pavel A.

AU - Rostovskii, Nikolai V.

AU - Khlebnikov, Alexander F.

AU - Khoroshilova, Olesya V.

AU - Novikov, Mikhail S.

PY - 2019/7/11

Y1 - 2019/7/11

N2 - A catalytic nucleophilic addition reaction of 3-hydroxybenzofuran-2-carboxylic acid derivatives to 2H-azirines for the high-yield synthesis of NH-aziridines with a 3-coumaranone substituent has been developed. The Ph 3 PAuNTf 2 -catalyzed reaction is diastereoselective to give predominantly (RS,SR)-isomer of aziridine in good yield. The Ni(hfacac) 2 -catalyzed reaction affords aziridines in up to 98% yield and low or moderate diastereoselectivity, which in some cases is opposite to that observed for the gold(I)-catalyzed reaction. The Ph 3 PAuNTf 2 works well for sterically hindered azirines as well as benzofurans bearing electron-withdrawing groups, whereas Ni(hfacac) 2 is the catalyst of choice for the preparation of aziridines having diazoacetyl substituent. The latter compounds can serve as substrates for the synthesis of fused aziridines via Buchner ring expansion reaction. (Figure presented.).

AB - A catalytic nucleophilic addition reaction of 3-hydroxybenzofuran-2-carboxylic acid derivatives to 2H-azirines for the high-yield synthesis of NH-aziridines with a 3-coumaranone substituent has been developed. The Ph 3 PAuNTf 2 -catalyzed reaction is diastereoselective to give predominantly (RS,SR)-isomer of aziridine in good yield. The Ni(hfacac) 2 -catalyzed reaction affords aziridines in up to 98% yield and low or moderate diastereoselectivity, which in some cases is opposite to that observed for the gold(I)-catalyzed reaction. The Ph 3 PAuNTf 2 works well for sterically hindered azirines as well as benzofurans bearing electron-withdrawing groups, whereas Ni(hfacac) 2 is the catalyst of choice for the preparation of aziridines having diazoacetyl substituent. The latter compounds can serve as substrates for the synthesis of fused aziridines via Buchner ring expansion reaction. (Figure presented.).

KW - diazo compounds

KW - gold

KW - nickel

KW - nitrogen heterocycles

KW - oxygen heterocycles

KW - Small ring systems

KW - INTERMOLECULAR NITRENE TRANSFER

KW - DOMINO REACTION

KW - VINYL AZIDES

KW - ISOMERIZATION

KW - REACTIVITY

KW - TERMINAL ALKYNES

KW - PHOSPHONATES

KW - BIOLOGICAL EVALUATION

KW - STEREOSELECTIVE-SYNTHESIS

KW - INHIBITORS

UR - http://www.scopus.com/inward/record.url?scp=85065513166&partnerID=8YFLogxK

UR - http://www.mendeley.com/research/transition-metalcatalyzed-synthesis-3coumaranonecontaining-nhaziridines-2hazirines-nickelii-versus-g

U2 - 10.1002/adsc.201900366

DO - 10.1002/adsc.201900366

M3 - Article

AN - SCOPUS:85065513166

VL - 361

SP - 3359

EP - 3372

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 14

ER -