Conjugate addition-enantioselective protonation to forge tertiary stereocentres α to azaarenes via cooperative hydrogen atom transfer and chiral hydrogen-bonding catalysis

doi:10.1016/S1872-2067(21)63887-1

Abstract

Abstract:

Cooperative hydrogen atom transfer and chiral hydrogen-bonding catalysis as a new platform for the asymmetric synthesis of azaarene derivatives is reported. By using a tetrabutylammonium decatungstate as the photocatalyst and a chiral phosphoric acid as the hydrogen-bonding catalyst, transformations of a variety of commercially available hydrocarbons and silanes with diverse α-branched 2-vinylazaarenes could efficiently experience a tandem radical conjugate addition and enantioselective protonation process, providing a convenient and fully atom economical approach to access a range of valuable enantioenriched α-tertiary azaarenes in high yields with good to excellent enantioselectivities (up to 93% ee). Through the direct use of tert-butyl methylcarbamate as the feedstock, this method enables a highly practical and concise synthesis of the enantiomerically pure medicinal molecule pheniramine (Avil).

Key words: Photocatalysis, Cooperative catalysis, Hydrogen atom transfer, Enantioselective protonation, Azaarenes

Yaqi Tan, Yanli Yin, Shanshan Cao, Xiaowei Zhao, Guirong Qu, Zhiyong Jiang. Conjugate addition-enantioselective protonation to forge tertiary stereocentres α to azaarenes via cooperative hydrogen atom transfer and chiral hydrogen-bonding catalysis[J]. Chinese Journal of Catalysis, 2022, 43(3): 558-563.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(21)63887-1

https://www.cjcatal.com/EN/Y2022/V43/I3/558

Figures/Tables 6

Scheme 1. Development of asymmetric photocatalytic protocols to access enantioenriched azaarene derivatives.

Table 1 Optimization of the reaction conditions a.

Entry	Variation from standard conditions	Yield^b (%)	ee ^c (%)
1	none	98	93
2	C30 instead of C46	94	4
3	C39 instead of C46	90	55
4	PhCl instead of CH₃CN	0^d	N.A.
5	EtOH instead of CH₃CN	0^d	N.A.
6	at 25 °C	95	78
7	no C46	94	N.A.
8	no TBADT	0^d	N.A.
9	no light	0^d	N.A.
10	under air	0^e	N.A.

Table 2 Transformations of hydrocarbons and silanes with α-branched 2-vinylpyridines a.

Table 3 Transformations of cyclohexane with α-phenyl 2-vinylazaarenes a.

Scheme 2. Synthesis of enantioenriched pheniramine.

Scheme 3. Mechanistic studies and the proposed mechanism.

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