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Review
. 2024 May 22;29(11):2442.
doi: 10.3390/molecules29112442.

Strategies for Accessing cis-1-Amino-2-Indanol

Inès Mendas  1 , Stéphane Gastaldi  1 , Jean-Simon Suppo  1
Affiliations
Review

Strategies for Accessing cis-1-Amino-2-Indanol

Inès Mendas et al. Molecules. .

Abstract

cis-1-amino-2-indanol is an important building block in many areas of chemistry. Indeed, this molecule is currently used as skeleton in many ligands (BOX, PyBOX…), catalysts and chiral auxiliaries. Moreover, it has been incorporated in numerous bioactive structures. The major issues during its synthesis are the control of cis-selectivity, for which various strategies have been devised, and the enantioselectivity of the reaction. This review highlights the various methodologies implemented over the last few decades to access cis-1-amino-2-indanol in racemic and enantioselective manners. In addition, the various substitution patterns on the aromatic ring and their preparations are listed.

Keywords: C-H activation; Ritter reaction; chemical resolution; cis-1-amino-2-indanol; enantioselective reaction; enzymatic resolution; epimerization; intramolecular cyclization.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Scheme 1
Scheme 1
cis-1-amino-2-indanol structure and examples of applications.
Scheme 2
Scheme 2
Main strategies developed for the synthesis of cis-1-amino-2-indanol.
Scheme 3
Scheme 3
Ritter type reaction from indene oxide.
Scheme 4
Scheme 4
Enantioselective synthesis of (1S,2R)-1-amino-2-indanol via the Ritter process.
Scheme 5
Scheme 5
Proposed mechanism for Ritter type reaction from epoxide.
Scheme 6
Scheme 6
Ritter type reaction from diols.
Scheme 7
Scheme 7
Ritter type reaction from indene under electrophotocatalytic conditions.
Scheme 8
Scheme 8
Proposed mechanism for Ritter type reaction from indene under electrophotocatalytic conditions.
Scheme 9
Scheme 9
Racemic synthesis of 1 through intramolecular amide cyclization.
Scheme 10
Scheme 10
Sepracor synthesis of enantiopure (1S,2R)-1-amino-2-indanol 1.
Scheme 11
Scheme 11
Ghosh synthesis of the two enantiomers of cis-1-amino-2-indanol.
Scheme 12
Scheme 12
Didier synthesis of the two enantiomers of cis-1-amino-2-indanol.
Scheme 13
Scheme 13
cis-1-amino-2-indanol from indene by iodoamidation.
Scheme 14
Scheme 14
Telluric anhydride-induced formation of oxazolidinone.
Scheme 15
Scheme 15
Recent approaches to the amino-oxygenation of indene.
Scheme 16
Scheme 16
General mechanism of indene amino-oxygenation.
Scheme 17
Scheme 17
Radical-mediated C–N bond formation.
Scheme 18
Scheme 18
First enantioselective radical-mediated C1-N functionalization.
Scheme 19
Scheme 19
MOF-supported copper-catalyzed oxazoline formation.
Scheme 20
Scheme 20
Copper-mediated intramolecular Csp3-H amination via radical pathway.
Scheme 21
Scheme 21
Approaches involving a nitrene intermediate.
Scheme 22
Scheme 22
Meggers’ approach to the synthesis of cis-1-amino-2-indanol.
Scheme 23
Scheme 23
Resnick’s synthesis of cis-1-amino-2-indanol.
Scheme 24
Scheme 24
Synthesis of enantiopure cis-1-amino-2-indanol via resolution of the corresponding azido-alcohol.
Scheme 25
Scheme 25
Synthesis of (1S,2R)-1 from 2-hydroxy-1-indanone.
Scheme 26
Scheme 26
Synthesis of 1 from 1,2-indanedion-1-oxime.
Scheme 27
Scheme 27
Ko’s synthesis of cis-1-amino-2-indanol.
Scheme 28
Scheme 28
Synthesis of cis-1-amino-2-indanol from 7,3-xylofuranose derivative.
Scheme 29
Scheme 29
Synthesis of cis-1-amino-2-indanol from D-phenylalanine.
Scheme 30
Scheme 30
Chemical resolution of racemic cis-1-amino-2-indanol.
Scheme 31
Scheme 31
Kawabata’s kinetic resolution via enantioselective acylation.
Scheme 32
Scheme 32
Resolution of cis-1-amino-2-indanol via diastereomeric salt formation.
Scheme 33
Scheme 33
R selective enzymatic acylation of N-Cbz protected racemic cis-1-amino-2-indanol.
Scheme 34
Scheme 34
R selective enzymatic hydrolysis of N,O-Ac protected racemic cis-1-amino-2-indanol.
Scheme 35
Scheme 35
Continuous-flow kinetic resolution of cis-1-amino-2-indanol with Novozym 435.
Scheme 36
Scheme 36
General strategy of post-functionalization.
Scheme 37
Scheme 37
General strategy of pre-functionalization.
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