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| Content Provider | PubMed Central |
|---|---|
| Author | Zsolt, Szakonyi Sillanpää, Reijo Fülöp, Ferenc |
| Editor | Stefan, Bräse |
| Copyright Year | 2014 |
| Abstract | 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 and, 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. |
| Related Links | http://dx.doi.org/10.3762/bjoc.10.289 |
| Ending Page | 2742 |
| Page Count | 5 |
| Starting Page | 2738 |
| File Format | |
| ISSN | 18605397 |
| e-ISSN | 18605397 |
| Journal | Beilstein Journal of Organic Chemistry |
| Volume Number | 10 |
| Language | English |
| Publisher | Beilstein-Institut |
| Publisher Date | 2014-11-01 |
| Access Restriction | Open |
| Rights Holder | Beilstein-Institut |
| Subject Keyword | Organic Chemistry Research in Higher Education |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry |
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