Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group

C.S. Lood; A.E. Laine; A. Högnäsbacka; M. Nieger; A.M.P Koskinen

doi:10.1002/ejoc.201500391

Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group

C.S. Lood, A.E. Laine, A. Högnäsbacka, M. Nieger, A.M.P Koskinen

Research output: Contribution to journal › Article › Scientific › peer-review

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Abstract

Tetrahydro-β-carbolines, a privileged structural feature in natural products and pharmaceutically active compounds, has been the cause for considerable research interest, spanning many decades. Herein is reported the synthesis of
the structurally closely related compounds denoted as (indol-2-yl)methanamines, in 99% ee using amino acid starting materials, coupled with a 9-phenyl-9-fluorenyl (Pf) protecting group strategy. Furthermore a conformational study of Pfprotected α-amino carbonyl compounds were undertaken by means of DFT refined molecular mechanics calculation, Xray crystallography measurements and NMR experiments in
order to elucidate the stereochemical protecting properties induced by the Pf group.

Original language	English
Pages (from-to)	3793-3805
Journal	European Journal of Organic Chemistry
Volume	2015
Issue number	17
DOIs	https://doi.org/10.1002/ejoc.201500391
Publication status	Published - 2015
MoE publication type	A1 Journal article-refereed

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ms179 EJOC 2015 3793Accepted author manuscript, 1.48 MB

CCDC 1036705: Experimental Crystal Structure Determination
Högnäsbacka, A. (Contributor), Koskinen, A. (Creator), Laine, A. (Creator), Lood, C. (Contributor) & Nieger, M. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2015
DOI: 10.5517/cc13ss3s, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13ss3s&sid=DataCite
Dataset
CCDC 1036700: Experimental Crystal Structure Determination
Högnäsbacka, A. (Contributor), Koskinen, A. (Creator), Laine, A. (Creator), Lood, C. (Contributor) & Nieger, M. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2015
DOI: 10.5517/cc13sryl, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13sryl&sid=DataCite
Dataset
CCDC 1036698: Experimental Crystal Structure Determination
Högnäsbacka, A. (Contributor), Koskinen, A. (Creator), Laine, A. (Creator), Lood, C. (Contributor) & Nieger, M. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2015
DOI: 10.5517/cc13srwj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13srwj&sid=DataCite
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@article{1eba6b460a1147a3ad93df339e782f36,

title = "Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group",

abstract = "Tetrahydro-β-carbolines, a privileged structural feature in natural products and pharmaceutically active compounds, has been the cause for considerable research interest, spanning many decades. Herein is reported the synthesis ofthe structurally closely related compounds denoted as (indol-2-yl)methanamines, in 99% ee using amino acid starting materials, coupled with a 9-phenyl-9-fluorenyl (Pf) protecting group strategy. Furthermore a conformational study of Pfprotected α-amino carbonyl compounds were undertaken by means of DFT refined molecular mechanics calculation, Xray crystallography measurements and NMR experiments inorder to elucidate the stereochemical protecting properties induced by the Pf group.",

author = "C.S. Lood and A.E. Laine and A. H{\"o}gn{\"a}sbacka and M. Nieger and A.M.P Koskinen",

year = "2015",

doi = "10.1002/ejoc.201500391",

language = "English",

volume = "2015",

pages = "3793--3805",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "WILEY-BLACKWELL",

number = "17",

}

Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group. / Lood, C.S.; Laine, A.E.; Högnäsbacka, A.; Nieger, M.; Koskinen, A.M.P.

In: European Journal of Organic Chemistry, Vol. 2015, No. 17, 2015, p. 3793-3805.

Research output: Contribution to journal › Article › Scientific › peer-review

TY - JOUR

T1 - Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group

AU - Lood, C.S.

AU - Laine, A.E.

AU - Högnäsbacka, A.

AU - Nieger, M.

AU - Koskinen, A.M.P

PY - 2015

Y1 - 2015

N2 - Tetrahydro-β-carbolines, a privileged structural feature in natural products and pharmaceutically active compounds, has been the cause for considerable research interest, spanning many decades. Herein is reported the synthesis ofthe structurally closely related compounds denoted as (indol-2-yl)methanamines, in 99% ee using amino acid starting materials, coupled with a 9-phenyl-9-fluorenyl (Pf) protecting group strategy. Furthermore a conformational study of Pfprotected α-amino carbonyl compounds were undertaken by means of DFT refined molecular mechanics calculation, Xray crystallography measurements and NMR experiments inorder to elucidate the stereochemical protecting properties induced by the Pf group.

AB - Tetrahydro-β-carbolines, a privileged structural feature in natural products and pharmaceutically active compounds, has been the cause for considerable research interest, spanning many decades. Herein is reported the synthesis ofthe structurally closely related compounds denoted as (indol-2-yl)methanamines, in 99% ee using amino acid starting materials, coupled with a 9-phenyl-9-fluorenyl (Pf) protecting group strategy. Furthermore a conformational study of Pfprotected α-amino carbonyl compounds were undertaken by means of DFT refined molecular mechanics calculation, Xray crystallography measurements and NMR experiments inorder to elucidate the stereochemical protecting properties induced by the Pf group.

U2 - 10.1002/ejoc.201500391

DO - 10.1002/ejoc.201500391

M3 - Article

VL - 2015

SP - 3793

EP - 3805

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 17

ER -

Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group

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Datasets

CCDC 1036705: Experimental Crystal Structure Determination

CCDC 1036700: Experimental Crystal Structure Determination

CCDC 1036698: Experimental Crystal Structure Determination

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