23963-70-4Relevant articles and documents
Stereoselective synthesis of perillaldehyde-based chiral β-amino acid derivatives through conjugate addition of lithium amides
Szakonyi, Zsolt,Sillanp??, Reijo,Fül?p, Ferenc
supporting information, p. 2738 - 2742 (2015/02/19)
The Michael addition of dibenzylamine to (+)- tert-butyl perillate ( 3) and to (+)- tert-butyl phellandrate (6), derived from ( S)-(-)-perillaldehyde (1 ), resulted in diastereomeric β-amino esters 7A-D in a moderately stereospecific reaction in a ratio of 76:17:6:1. After separation of the diastereoisomers, the major product, cis isomer 7A, was quantitatively isomerized to the minor component, trans-amino ester 7D. All four isomers were transformed to the corresponding β-amino acids 10A-D, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles in three steps. The steric effects of the isopropyl group at position 4 and of the α-methyl substituent of (R)-N-benzyl-N-α-methylbenzylamine on the reactivity were also studied, upon application of a chiral amine, excellent stereoselectivity of the conjugate addition was observed. Amino ester 11 was obtained as a single product and transformed to the corresponding amino acids 10A and 10D in good yields on the gram scale.
Absolute configuration of a new mosquito repellent, (+)-eucamalol and the repellent activity of its epimer.
Satoh,Utamura,Nakade,Nishimura
, p. 1139 - 1141 (2007/10/02)
(+)-Eucamalol (1) and (-)-1-epi-eucamalol (2) were synthesized from (S)-(-)-perillaldehyde to determine the absolute configuration of 1, the structure of natural (+)-eucamalol being determined to be (1R,6R)-(+)-3-formyl-6-isopropyl-2-cyclohexen-1-ol. (+)-
