Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide

doi:10.6023/cjoc202303035

Abstract

An organocatalytic enantioselective direct vinylogous allylic alkylation between coumarins and racemic Morita- Baylis-Hillman carbonates has been developed. With 10~15 mol% a chiral cyclohexane-based phosphine-amide C10, a wide range of densely functionalized coumarin derivatives have been achieved in 87%~99% yields and up to 98% ee.

Key words: allylic alkylation, asymmetric catalysis, chiral phosphine, organocatalysis, vinylogous reaction

Cite this article

Chun-Xia Cheng, Lu-Ping Wu, Feng Sha, Xin-Yan Wu. Enantioselective Vinylogous Allylic Alkylation of Coumarins with Morita-Baylis-Hillman Carbonates Catalyzed by Chiral Phosphine-Amide[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3188-3195.

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Entry	R¹	R²	R³	Time/h	3	Yield^b/%	ee^c/%
1	H	4-Cl	Me	9	3a	90	90
2	H	4-Cl	Et	24	3b	89	86
3	H	4-Cl	ⁿBu	24	3c	92	87
4	H	4-Cl	Bn	36	3d	94	88
5	H	4-Cl	^tBu	24	3e	97	93
6	H	H	^tBu	30	3f	85 (96)	92
7	H	4-NO₂	^tBu	24	3g	74 (99)	96
8	H	4-Br	^tBu	24	3h	94	94
9	H	4-F	^tBu	24	3i	91	90
10	H	4-Me	^tBu	36	3j	80 (93)	93
11	H	3-Br	^tBu	24	3k	91	90
12	H	2-Br	^tBu	24	3l	70 (93)	98
13	6-Br	4-Cl	^tBu	48	3m	70 (89)	94
14	7-Br	4-Cl	^tBu	48	3n	72 (87)	95
15	7-OMe	4-Cl	^tBu	48	3o	83 (98)	90

Entry	R¹	R²	R³	Time/h	3	Yield^b/%	ee^c/%
1	H	4-Cl	Me	9	3a	90	90
2	H	4-Cl	Et	24	3b	89	86
3	H	4-Cl	ⁿBu	24	3c	92	87
4	H	4-Cl	Bn	36	3d	94	88
5	H	4-Cl	^tBu	24	3e	97	93
6	H	H	^tBu	30	3f	85 (96)	92
7	H	4-NO₂	^tBu	24	3g	74 (99)	96
8	H	4-Br	^tBu	24	3h	94	94
9	H	4-F	^tBu	24	3i	91	90
10	H	4-Me	^tBu	36	3j	80 (93)	93
11	H	3-Br	^tBu	24	3k	91	90
12	H	2-Br	^tBu	24	3l	70 (93)	98
13	6-Br	4-Cl	^tBu	48	3m	70 (89)	94
14	7-Br	4-Cl	^tBu	48	3n	72 (87)	95
15	7-OMe	4-Cl	^tBu	48	3o	83 (98)	90

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手性叔膦-酰胺不对称催化香豆素与Morita-Baylis-Hillman碳酸酯之间的插烯烯丙基烷基化反应