Formal Total Syntheses of (+)- and (-)-ar-Macrocarpene via Rh(I)-BINAP Catalyzed Conjugate Addition

被引：0

作者：

Khatua, Arindam ^{[1
]}

Pal, Souvik ^{[1
]}

Bisai, Vishnumaya ^{[1
,2
,3
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal Bypass Rd, Bhopal 462066, Madhya Pradesh, India

[2] Indian Inst Sci Educ & Res Tirupati, Dept Chem, Transit Campus,Karkambadi Rd, Tirupati 517507, Andhra Pradesh, India

[3] Indian Inst Sci Educ & Res Berhampur, Dept Chem Sci, Transit Campus,Engn Sch Junct Govt ITI Bldg, Berhampur 760010, Odisha, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 16期

关键词：

Conjugate addition; (p-Tolyl)boronic acid; Rh-(I)-catalysis; Sesquiterpenoid; ar-Macrocarpene; ASYMMETRIC 1,4-ADDITION; SESQUITERPENES; ACIDS; CHEMISTRY;

D O I：

10.1002/ejoc.202000100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalytic asymmetric formal total syntheses of both antipodes of sesquiterpene, (+)-ar-macrocarpene (1) and (-)-ar-macrocarpene (ent-1) has been achieved from 5,5-dimethyl-(3-p-tolyl)cyclohexanone 12. Enantioenriched compound 12 was obtained in excellent yield with 96 % ee by catalytic enantioselective p-tolylboronic acid addition to 5,5-dimethyl cyclohexen-2-one 13 using Rh-(I)-(S)-BINAP (L7). Moreover, ent-12 was achieved in 96 % ee by using Rh-(I)-(R)-BINAP (ent-L7).

引用

页码：2435 / 2438

页数：4

共 37 条

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