Formal Total Syntheses of (+)‐ and (–)‐ ar ‐Macrocarpene via Rh (I) ‐BINAP Catalyzed Conjugate Addition | Zendy

Khatua Arindam | Zendy; Pal Souvik | Zendy; Bisai Vishnumaya | Zendy

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

Author(s) -

Khatua Arindam,

Pal Souvik,

Bisai Vishnumaya

Publication year - 2020

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202000100

Subject(s) - chemistry , enantioselective synthesis , binap , cyclohexanone , conjugate , catalysis , yield (engineering) , stereochemistry , total synthesis , medicinal chemistry , organic chemistry , mathematical analysis , mathematics , materials science , metallurgy

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 ).

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