In:
European Journal of Organic Chemistry, Wiley, Vol. 2019, No. 7 ( 2019-02-21), p. 1594-1599
Abstract:
The d and l amino acid mediated enantioselective intramolecular aldol reaction of 4‐((1‐methyl‐2,6‐dioxo‐cyclohexyl)methyl)‐pent‐4‐enal 1 leading, after dehydration, to (‐)‐( R ) and (+)‐( S ) 4a‐methyl‐3‐methylene‐5‐oxo‐2,3,4,4a,5,6,7,8‐octahydro‐naphthalene‐1‐carbaldehyde 2 was explored. It was found that (‐)‐( R ) carbaldehyde 2 is enantioselectively formed in the presence of l ‐amino acids while (+)‐( S ) carbaldehyde 2 is enantioselectively formed in the presence of d ‐amino acids. (‐)‐( R ) Carbaldehyde 2 was then transformed into ( + )‐ 22 . The absolute configuration and relative stereochemistry of the latter was established by single‐crystal X‐ray diffraction analysis of p ‐iodobenzoate ( + )‐ 23 .
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2019.7
DOI:
10.1002/ejoc.201801771
Language:
English
Publisher:
Wiley
Publication Date:
2019
detail.hit.zdb_id:
1475010-7