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. 1998 Jul;1998(7):937-961.

doi: 10.1055/s-1998-2092.

cis-1-Aminoindan-2-ol in Asymmetric Syntheses

Arun K Ghosh¹, Steve Fidanze¹, Chris H Senanayake²

Affiliations

Affiliations

¹ Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA.
² Sepracor Inc, Chemical Research and Development, 111 Locke Drive, Marlbrough, MA 01752, USA Fax +1(312)9960431; arun.ghosh@uic.edu.

PMID: 30393403
PMCID: PMC6214626
DOI: 10.1055/s-1998-2092

cis-1-Aminoindan-2-ol in Asymmetric Syntheses

Arun K Ghosh et al. Synthesis (Stuttg). 1998 Jul.

. 1998 Jul;1998(7):937-961.

doi: 10.1055/s-1998-2092.

Authors

Arun K Ghosh¹, Steve Fidanze¹, Chris H Senanayake²

Affiliations

¹ Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607, USA.
² Sepracor Inc, Chemical Research and Development, 111 Locke Drive, Marlbrough, MA 01752, USA Fax +1(312)9960431; arun.ghosh@uic.edu.

PMID: 30393403
PMCID: PMC6214626
DOI: 10.1055/s-1998-2092

Abstract

A review on cis-1-aminoindan-2-ol derived asymmetric syntheses is described.

Keywords: 1-aminoindan-2-ol; asymmetric synthesis; inhibitor; protease.

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Figures

Figure 1. — Figure 1.
Auxiliaries and Catalysts Used in Asymmetric Synthesis

Figure 2. — Figure 2.
Zimmerman-Traxler Type Transition States

Figure 3. — Figure 3.
Conformations 101 and 102 During L-Selectride Reduction

Figure 4. — Figure 4.
Transition States 125 and 126

Figure 5. — Figure 5.
Transition Models 148 and 149

Figure 6. — Figure 6.
Structures of Inhibitors 167–169

Figure 7. — Figure 7.
Structures of Different Dipeptide Isosteres

Figure 8. — Figure 8.
Structural Features of Indinavir (180)

Figure 9. — Figure 9.
Structures of 193–195

Scheme 1 — Scheme 1

Scheme 2 — Scheme 2

Scheme 3 — Scheme 3

Scheme 4 — Scheme 4

Scheme 5 — Scheme 5

Scheme 6 — Scheme 6

Scheme 7 — Scheme 7

Scheme 8 — Scheme 8

Scheme 9 — Scheme 9

Scheme 10 — Scheme 10

Scheme 11 — Scheme 11

Scheme 12 — Scheme 12

Scheme 13 — Scheme 13

Scheme 14 — Scheme 14

Scheme 15 — Scheme 15

Scheme 16 — Scheme 16

Scheme 17 — Scheme 17

Scheme 18 — Scheme 18

Scheme 19 — Scheme 19

Scheme 20 — Scheme 20

Scheme 21 — Scheme 21

Scheme 22 — Scheme 22

Scheme 23 — Scheme 23

Scheme 24 — Scheme 24

Scheme 25 — Scheme 25

Scheme 26 — Scheme 26

Scheme 27 — Scheme 27

Scheme 28 — Scheme 28

Scheme 29 — Scheme 29

Scheme 30 — Scheme 30

Scheme 31 — Scheme 31

Scheme 32 — Scheme 32

Scheme 33 — Scheme 33

Scheme 34 — Scheme 34

Scheme 35 — Scheme 35

Scheme 36 — Scheme 36

Scheme 37 — Scheme 37

Scheme 38 — Scheme 38

Scheme 39 — Scheme 39

Scheme 40 — Scheme 40

Scheme 41 — Scheme 41

Scheme 42 — Scheme 42

Scheme 43 — Scheme 43

Scheme 44 — Scheme 44

Scheme 45 — Scheme 45

Scheme 46 — Scheme 46

Scheme 47 — Scheme 47

Scheme 48 — Scheme 48

Scheme 49 — Scheme 49

Scheme 50 — Scheme 50

See this image and copyright information in PMC

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References

1. For recent reviews, see: Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Seyden-Penne J, Ed.; Wiley Interscience: New York, 1995.Stereoselective Synthesis; Nogradi M, Ed.; VCH Publishers: New York, 1995.Asymmteric Catalysis in Organic Synthesis, Noyori R; Wiley Interscience: New York, 1994.Catalytic Asymmetric Synthesis; Ojima I, Ed.; VCH Publishers: New York, 1993, and references cited therein.
1. Takaya H; Ohta T; Noyori R Asymmetric hydrogenation In Catalytic Asymmetric Synthesis; Ojima I, Ed.; VCH Publishers: New York, 1993; pp 1–39.
1. Kolb HC; VanNieuwenhze MS; Sharpless KB Chem. Rev 1994, 94, 2483.
2. Johnson RA; Sharpless KB In Catalytic Asymmetric Synthesis; Ojima I, Ed.; VCH Publishers: New York, 1993; pp 227–272.
3. Lohray BB Tetrahedron: Asymmetry 1992, 3, 1317, and references cited therein.
1. Sharpless KB Tetrahedron 1994, 50, 4235.
2. Johnson RA; Sharpless KB In Catalytic Asymmetric Synthesis; Ojima I, Ed.; VCH Publishers: New York, 1993; pp 103–158.
1. Jacobsen EN In Catalytic Asymmetric Synthesis; Ojima I, Ed.; VCH Publishers: New York, 1993; pp 159–202.

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