Amino acids as a chiral pool: Synthesis of (S)- and (R)-2-N-carbomethoxy-5- aminoindane from (S)- and (R)-phenylalanines

Synthetic Communications

Volumn 37, Issue 9, 2007, Pages 1445-1454

  Waykole, Liladhar M ^a   McKenna, Joseph J ^a   Bach, Andrew ^a   Prashad, Mahavir ^a   Repič, Oljan ^a   Blacklock, Thomas J ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Amino acids; Aminoindane; Chiral pool; Phenylalanine

Indexed keywords

2 N CARBOMETHOXY 5 AMINOINDANE; AMINO ACID DERIVATIVE; HYDROXYL GROUP; INDAN DERIVATIVE; INDANONE DERIVATIVE; PHENYLALANINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; HYDROGENATION; NITRATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34248548645     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701226905     Document Type: Article

References (11)

1. (a) Senanayake, C. H. Applications of cis-1-amino-2-indanol in asymmetric synthesis. Aldrachimica Acta 1998, 31 (1), 3-15;
2. (b) Kozhushkov, S. I.; Yufit, D. S.; Meijere, A. Convenient and inexpensive synthesis of (1R, 2R)-trans-1-amino-6- nitroindan-2-ol. Adv. Synth. Catal. 2005, 347, 255-265.
3. (a) Fink, C.; Ksander, G.; Kukkola, P.; Prashad, M. Preparation of N-benzocycloalkyl-amides as inhibitors or microsomal triglyceride transfer protein (MTP) and apolipoprotein B (ApoB) secretion, U.S. Patent 6,197,798, March 6, 2001;
4. (b) Ksander, G. M.; de Jesus, R. .; Yuan, A.; Fink, C.; Moskal, M.; Carlson, E.; Kukkola, P.; Bilci, N.; Wallace, E.; Neubert, A.; Feldman, D.; Mogelesky, T.; Poirier, K.; Jeune, M.; Steele, R.; Wasvery, J.; Stephan, Z.; Cahill, E.; Webb, R.; Navarrete, A.; Lee, W.; Gibson, J.; Alexander, N.; Sharif, H.; Hospattankar, A. Diaminoindane as microsomal triglyceride transfer protein inhibitors. J. Med. Chem. 2001, 44, 4677-4687.
5. (a) Fink, C.; Ksander, G. M.; Kukkola, P. J.; Wallace, E. Preparation of N-benzocycloalkyl-amides as inhibitors or microsomal triglyceride transfer protein (MTP) and apolipoprotein B (ApoB) secretion. WO 0005201, February 3, 2000;
6. (b) Prashad, M.; Hu, B.; Har, D.; Repič, O.; Blacklock, T. J. Efficient and practical syntheses of (R)-(5-amino-2,3-dihydro-1H- inden-2-yl)-carbamic acid methyl ester. Adv. Synth. Catal. 2001, 343, 461-472.
7. Dornhege, E. Liebigs Ann. Chem. 1971, 743, 42.
8. McClure, D. E.; Arison, B. H.; Blawin, J. J. Chiral α-amino ketone from the Friedel-Crafts reaction of protected amino acids. J. Org. Chem. 1981, 46, 2431-2433.
9. McClure, D. E.; Lumma, P. K.; Arison, B. H.; Jones, J. H.; Baldwin, J. 1,4-Oxazines via intramolecular ring closure of β-hydroxydiaoacetamide: Phenyalanine to tetrahydroindeno [1,2-b]-1,4-oxazin-3(2H)-ones. J. Org. Chem. 1983, 48, 2675-2679.
10. Buckley, T. F., III; Rapoport, H. α-Amino acids as chiral educts for asymmetric products. Amino acylation with N-acylamino acids. J. Am. Chem. Soc. 1981, 103, 6157-6163.
11. Petri, E. M.; Staverman, A. J. Recl. Trav. Chim. Pays-Bas 1952, 71, 385.