手性膦酸催化剂最新应用盘点
2023-05-30 · 系列介绍 · 百灵威授权转载
手性膦酸（CPAs）是一类用途广泛的Brønsted酸有机催化剂，近年来在不对称合成中的应用范围不断扩大。本文参考相关文献[1]，总结了手性膦酸催化剂在不对称合成领域最新应用进展。
![图2 对映体选择性构建氮杂螺环的三组分Povarov反应<sup>[2]</sup>](/assets/jk-articles-all/8be95730a7cfed7c9d5487c2.svg)
![图3 手性膦酸催化的Minisci反应<sup>[3]</sup>](/assets/jk-articles-all/21a021a5035becc9c3ce5f25.svg)
![图4 手性膦酸催化α-氨基酯去乙酰化反应<sup>[4]</sup>](/assets/jk-articles-all/13b64ad6d0ec7b3096ad7493.svg)
![图5 手性膦酸催化亲核取代合成手性3,3’-, 3,2’-和3,1’-双(吲哚基)甲烷<sup>[5]</sup>](/assets/jk-articles-all/5058fc3fd5d6079d8c6fe2fe.svg)
![图6 手性膦酸催化不对称Diels-Alder反应<sup>[6]</sup>](/assets/jk-articles-all/c34981000bb28d504f2a389f.svg)
![图7 手性膦酸催化氧杂环丁烷合成手性吡咯烷<sup>[7]</sup>](/assets/jk-solutions/6b7dd8a0e1f03db4aeec8c9e.svg)
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双功能手性方酰胺有机催化剂
不对称合成——只取所需，定向构建手性分子
图1 手性膦酸最新应用涉及催化剂结构及货号
多组分反应
图2 对映体选择性构建氮杂螺环的三组分Povarov反应[2]
光氧化还原反应
图3 手性膦酸催化的Minisci反应[3]
图4 手性膦酸催化α-氨基酯去乙酰化反应[4]
取代反应
图5 手性膦酸催化亲核取代合成手性3,3’-, 3,2’-和3,1’-双(吲哚基)甲烷[5]
加成反应
图6 手性膦酸催化不对称Diels-Alder反应[6]
重排反应
图7 手性膦酸催化氧杂环丁烷合成手性吡咯烷[7]
产品列表
| 品名 | CAS | 货号 |
|---|---|---|
| (11bS)-2,6-Di-9-phenanthrenyl-4-hydroxy-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 98%
(S)-3,3'-二-9-菲基-1,1'-联萘酚磷酸酯 | 1043567-32-3 | 2698516 |
| (11bR)-4-Hydroxy-2,6-bis(2,4,6-trimethylphenyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 98%
(R)-3,3'-双(2,4,6-三甲基苯基)-1,1'-联萘酚磷酸酯 | 695162-87-9 | 2698520 |
| (11bR)-4-Hydroxy-2,6-bis(2,3,4,5,6-pentafluorophenyl)-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 98%, ee: ≥99%
(R)-3,3'-双(2,3,4,5,6-五氟苯基)-1,1'-联萘酚磷酸酯 | 1284293-45-3 | 9108770 |
| (11bR)-2,6-Bis([1,1'-biphenyl]-4-yl)-4-hydroxy-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 98%
(R)-3,3'-双(4-苯基苯基)-1,1'-联萘酚磷酸酯 | 699006-54-7 | 9222328 |
| (11bR)-8,9,10,11,12,13,14,15-Octahydro-4-hydroxy-2,6-bis[4-(trifluoromethyl)phenyl]-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 98%, ee: ≥99%
(R)-3,3'-双(4-三氟甲基苯基)-5,5',6,6',7,7',8,8'-八氢-1,1'-联萘酚磷酸酯 | 791616-70-1 | 2772085 |
| (11aS)-10,11,12,13-Tetrahydro-5-hydroxy-3,7-bis[2,4,6-trisisopropylphenyl]-5-oxide-diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin, 98% (99% ee)
(11aS)-3,7-双[2,4,6-三(异丙基)苯基]-10,11,12,13-四氢-5-羟基-二茚并[7,1-de:1',7'-fg][1,3,2]二氧磷杂八环5-氧化物 | 1258276-28-6 | 15-0464 |
| (11aS)-3,7-Di-9-anthracenyl-10,11,12,13-tetrahydro-5-hydroxy-5-oxide-diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin, 98%, (99% ee)
(11aS)-3,7-二-9-蒽基-10,11,12,13-四氢-5-羟基-5-氧化物二茚并[7,1-de：1',7'-fg] [11,3,2] 二恶磷环庚烷 | 1393527-23-5 | 15-0335 |
参考文献
- Jiménez E I. An update on chiral phosphoric acid organocatalyzed stereoselective reactions[J]. Organic & Biomolecular Chemistry, 2023, 21(17): 3477-3502.
- Mo N F, Zhang Y, Guan Z H. Highly Enantioselective Three-Component Povarov Reaction for Direct Construction of Azaspirocycles[J]. Organic Letters, 2022, 24(35): 6397-6401.
- Liang D, Chen J R, Tan L P, et al. Catalytic asymmetric construction of axially and centrally chiral heterobiaryls by Minisci reaction[J]. Journal of the American Chemical Society, 2022, 144(13): 6040-6049.
- Chai X, Hu X, Zhao X, et al. Asymmetric Hydroaminoalkylation of Alkenylazaarenes via Cooperative Photoredox and Chiral Hydrogen‐Bonding Catalysis[J]. Angewandte Chemie, 2022, 134(10): e202115110.
- Zhu W R, Su Q, Deng X Y, et al. Organocatalytic enantioselective SN 1-type dehydrative nucleophilic substitution: access to bis (indolyl) methanes bearing quaternary carbon stereocenters[J]. Chemical Science, 2022, 13(1): 170-177.
- Zhu X Q, Wang Q, Zhu J. Organocatalytic Enantioselective Diels–Alder Reaction of 2‐Trifluoroacetamido‐1,3‐dienes with α,β‐Unsaturated Ketones[J]. Angewandte Chemie, 2023, 135(1): e202214925.
- Zhang R, Sun M, Yan Q, et al. Asymmetric Synthesis of Pyrrolidines via Oxetane Desymmetrization[J]. Organic Letters, 2022, 24(12): 2359-2364.
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