Four-Step One-Pot Catalytic Asymmetric Synthesis of Polysubstituted Tricyclic Compounds: Lipase-Catalyzed Dynamic Kinetic Resolution Followed by an Intramolecular Diels–Alder Reaction

Abstract

Starting from readily available tertiary alcohols, four different reactions (a 1,3-migration of a hydroxy group, kinetic resolution, racemization, and an intramolecular Diels–Alder reaction) took place under co-catalysis by lipase and oxovanadium compounds in a one-pot process to produce polysubstituted tricyclic carbon frameworks in high yields and with high enantioselectivities. The key to the success of this process was the discovery that a silyl group attached to the terminal carbon of the vinyl moiety completely controls the direction of hydroxy group migration

Key words

allylic alcohols - asymmetric synthesis - Diels–Alder reaction - dynamic kinetic resolution - lipase - one-pot reaction

Publication History

Received: 07 December 2020

Accepted after revision: 04 January 2021

Accepted Manuscript online:
04 January 2021

Article published online:
26 January 2021

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