Asymmetric synthesis of 1,3-diamines. II: Diastereoselective reduction of atropisomeric N-tert -butanesulfinylketimines

Marina Martjuga; Sergey Belyakov; Edvards Liepinsh; Edgars Suna

doi:10.1021/jo1025767

Asymmetric synthesis of 1,3-diamines. II: Diastereoselective reduction of atropisomeric N-tert -butanesulfinylketimines

Marina Martjuga
, Sergey Belyakov
, Edvards Liepinsh
, Edgars Suna^*

^*Corresponding author for this work

Latvian Institute of Organic Synthesis

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

26 Citations (Scopus)

Abstract

Chiral, nonracemic o-aminobenzylamines were prepared in a highly diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines. The ortho-substituent ensures the distinct reactivity of atropisomers 4d-f. The free energy of activation for atropisomerization of sulfinylimines 4d-f in THF-d₈ was determined by NMR methods to range from 70.8 to 97.9 kJ/mol.

Original language	English
Pages (from-to)	2635-2647
Journal	Journal of Organic Chemistry
Volume	76
Issue number	8
DOIs	https://doi.org/10.1021/jo1025767
Publication status	Published - 15 Apr 2011
Externally published	Yes

OECD Field of Science

1.4 Chemical Sciences

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10.1021/jo1025767

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title = "Asymmetric synthesis of 1,3-diamines. II: Diastereoselective reduction of atropisomeric N-tert -butanesulfinylketimines",

abstract = "Chiral, nonracemic o-aminobenzylamines were prepared in a highly diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines. The ortho-substituent ensures the distinct reactivity of atropisomers 4d-f. The free energy of activation for atropisomerization of sulfinylimines 4d-f in THF-d8 was determined by NMR methods to range from 70.8 to 97.9 kJ/mol.",

author = "Marina Martjuga and Sergey Belyakov and Edvards Liepinsh and Edgars Suna",

year = "2011",

month = apr,

day = "15",

doi = "10.1021/jo1025767",

language = "English",

volume = "76",

pages = "2635--2647",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Asymmetric synthesis of 1,3-diamines. II

T2 - Diastereoselective reduction of atropisomeric N-tert -butanesulfinylketimines

AU - Martjuga, Marina

AU - Belyakov, Sergey

AU - Liepinsh, Edvards

AU - Suna, Edgars

PY - 2011/4/15

Y1 - 2011/4/15

N2 - Chiral, nonracemic o-aminobenzylamines were prepared in a highly diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines. The ortho-substituent ensures the distinct reactivity of atropisomers 4d-f. The free energy of activation for atropisomerization of sulfinylimines 4d-f in THF-d8 was determined by NMR methods to range from 70.8 to 97.9 kJ/mol.

AB - Chiral, nonracemic o-aminobenzylamines were prepared in a highly diastereoselective reduction of atropisomeric N-tert-butanesulfinylketimines. The ortho-substituent ensures the distinct reactivity of atropisomers 4d-f. The free energy of activation for atropisomerization of sulfinylimines 4d-f in THF-d8 was determined by NMR methods to range from 70.8 to 97.9 kJ/mol.

UR - https://www.scopus.com/pages/publications/79953908279

UR - https://www.ncbi.nlm.nih.gov/pubmed/21410270

U2 - 10.1021/jo1025767

DO - 10.1021/jo1025767

M3 - Article

AN - SCOPUS:79953908279

SN - 0022-3263

VL - 76

SP - 2635

EP - 2647

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 8

ER -

Asymmetric synthesis of 1,3-diamines. II: Diastereoselective reduction of atropisomeric N-tert -butanesulfinylketimines

Abstract

OECD Field of Science

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