酰胺的“一瓶”催化不对称还原型Bischler-Napieralski反应: 生物活性1-取代四氢异喹啉的对映选择性合成

doi:10.6023/A25120419

摘要/Abstract

本工作采用先官能化再还原的酰胺不对称还原转化新策略实现了酰胺的“一瓶”催化不对称还原型Bischler-Napieralski反应. 该方法涉及串联进行的三氟甲磺酸酐/2-氟-吡啶(Tf₂O/2-F-Pyr.)促进的Bischler-Napieralski脱水环化以及水相Noyori型催化不对称转移氢化(CATH)反应. 通过此一瓶法, 以高收率和优异的对映选择性合成了一系列四氢异喹啉衍生物. 该方法适用于酰基部分带有给电子或吸电子基团的N-芳乙基芳香酰胺, 以及N-芳乙基脂肪酰胺. 通过这一方法实现了四个生物碱, (S)-猪毛菜定碱、(S)-劳丹素、(S)-木防己碱、(S)-N-norlaudanidine, 以及药物分子ACT-335827的高效、催化对映选择性合成. 此外, 还实现了生物碱(S)-cryptostyline III及药物分子almorexant等的形式合成.

关键词: 酰胺, 酰胺活化, 四氢异喹啉, 生物碱, 还原型Bischler-Napieralski反应, 催化不对称转移氢化, 催化不对称合成

Herein, we report the one-pot, catalytic asymmetric reductive Bischler-Napieralski-type reaction of amides as the first demonstration of a new strategy for the asymmetric reductive transformation of amides, which allowed for the one-pot, enantioselective access to tetrahydroisoquinoline (THIQ). The method features a tandem sequence involving the Tf₂O/2-F-Pyr.-promoted Bischler-Napieralski dehydracyclization and an aqueous Noyori-type catalytic asymmetric transfer hydrogenation (CATH). By this one-pot method, a variety of THIQ derivatives were synthesized in high yields and in excellent enantioselectivities. This protocol accommodates N-arylethyl aromatic amides bearing either electron-donating or electron-withdrawing groups on the acyl moiety, and N-arylethyl aliphatic amides. The synthetic utility of this methodology was demonstrated via the efficient, catalytic enantioselective synthesis of four alkaloids: (S)-salsolidine, (S)-laudanosine, (S)-xylopinine, and (S)-N-norlaudanidine, and medicinal agent ACT-335827. Additionally, formal syntheses of alkaloid (S)-cryptostyline III and medicinal agents such as almorexant were achieved.

Key words: amides, amide activation, tetrahydroisoquinolines, alkaloids, reductive Bischler-Napieralski-type reaction, catalytic asymmetric transfer hydrogenation, catalytic asymmetric synthesis

引用此文

卢广生, 韩增, 叶剑良, 黄培强. 酰胺的“一瓶”催化不对称还原型Bischler-Napieralski反应: 生物活性1-取代四氢异喹啉的对映选择性合成[J]. 化学学报, 2026, 84(4): 476-483.

Guangsheng Lu, Zeng Han, Jianliang Ye, Peiqiang Huang. One-pot, Catalytic Asymmetric Reductive Bischler-Napieralski-Type Reaction of Amides: An Enantioselective Entrance to Biologically Active 1-Substituted Tetrahydroisoquinolines[J]. Acta Chimica Sinica, 2026, 84(4): 476-483.

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图/表 7

Scheme 1. Strategies for the direct, catalytic asymmetric reductive functionalization of amides

Figure 1. Representative 1-substituted tetrahydroisoquinoline alkaloids and medicinal agents

Scheme 2. Initial attempts for a one-pot protocol integrating Bischler-Napieralski reaction with Noyori’s CATH

Entry	Variation from standard condition	Yield^a/%	ee^b/%
1	none	96	94
2	1 mol% (R,R)-NC	86	93
3	0.5 mol% (R,R)-NC	52	90
4	0.1 mol% (R,R)-NC	34	92
5	no Bi(OTf)₃	40	89
6	no AgSbF₆	33	91
7	3 mol% AgSbF₆, 6 mol% Bi(OTf)₃	65	89
8	2 mol% AgSbF₆, 4 mol% Bi(OTf)₃	45	91
9	20 equiv. HCOONa	73	90
10	10 equiv. HCOONa	65	89
11	40 equiv. HCOONa	93	92
12	HCOOK instead of HCOONa	13	90
13	HCOOLi instead of HCOONa	8	90
14	HCOONH₄ instead of HCOONa	49	89
15	r.t. for 18 h	85	92

Table 1. Optimization of reaction conditions

Table 2. Scope of amidesa

Scheme 3. One-step synthesis and formal synthesis of natural products and medicinal agents

Scheme 4. Synthesis of alkaloid (S)-N-norlaudanidine

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