In:
European Journal of Organic Chemistry, Wiley, Vol. 2020, No. 4 ( 2020-01-31), p. 420-423
Abstract:
A new strategy for the construction of vicinal stereocenters containing quaternary and tertiary carbons has been developed. The quaternary carbon center was constructed by an enantioselective intramolecular aldol reaction with an organocatalyst (Hua‐cat), and a [3.3.1]‐bicyclic compound was obtained in 81 % with 84 % ee . The absolute configuration of the bicyclic compound was determined by modified Mosher's method, and recrystallization of the p ‐bromobenzoate improved the ee to 99.5 %. Subsequent diastereoselective cyclopropanation of the double bond adjacent to the quaternary carbon gave rise to a [4.3.1.0]‐tricyclic product with a dr 〉 99:1. In addition, this method was applied to the formal synthesis of (–)‐chenopodene.
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2020.4
DOI:
10.1002/ejoc.201901722
Language:
English
Publisher:
Wiley
Publication Date:
2020
detail.hit.zdb_id:
1475010-7
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