Stereoselective a-alkylation of fully protected L-serine

Ari M.P. Koskinen; Pauli Saarenketo; Thomas Straub

doi:10.1002/ejoc.200400207

Stereoselective a-alkylation of fully protected L-serine

Ari M.P. Koskinen
, Pauli Saarenketo
, Thomas Straub

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

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Abstract

Diastereoselective alkylation of the (2S,4S) and (2R,4S) diastereomers of 3-tert-butyl 4-methyl 2-tert-butyl-1,3-oxazolidine-3,4-dicarboxylate (1a/b) is reported. Formation of both diastereomers of these oxazolidines was achieved by changing
the order of protection steps, and their relative and absolute configurations were determined by NOESY spectroscopy. The use of the bulky ring substituent tBu together with Boc as the N-protecting group led to the exclusive formation of only one alkylated diastereomer.

Original language	English
Pages (from-to)	3879-3883
Journal	European Journal of Organic Chemistry
DOIs	https://doi.org/10.1002/ejoc.200400207
Publication status	Published - 2004
MoE publication type	A1 Journal article-refereed

Keywords

L-serine
NOESY
stereoselective

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10.1002/ejoc.200400207

ms105Accepted author manuscript, 114 KB

CCDC 230045: Experimental Crystal Structure Determination
Koskinen, A. (Creator), Saarenketo, P. (Contributor) & Straub, T. (Contributor), Cambridge Crystallographic Data Centre , 1 Jan 2005
DOI: 10.5517/cc7qct3, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc7qct3&sid=DataCite
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title = "Stereoselective a-alkylation of fully protected L-serine",

abstract = "Diastereoselective alkylation of the (2S,4S) and (2R,4S) diastereomers of 3-tert-butyl 4-methyl 2-tert-butyl-1,3-oxazolidine-3,4-dicarboxylate (1a/b) is reported. Formation of both diastereomers of these oxazolidines was achieved by changing the order of protection steps, and their relative and absolute configurations were determined by NOESY spectroscopy. The use of the bulky ring substituent tBu together with Boc as the N-protecting group led to the exclusive formation of only one alkylated diastereomer.",

keywords = "L-serine, NOESY, stereoselective, L-serine, NOESY, stereoselective, L-serine, NOESY, stereoselective",

author = "Koskinen, \{Ari M.P.\} and Pauli Saarenketo and Thomas Straub",

year = "2004",

doi = "10.1002/ejoc.200400207",

language = "English",

pages = "3879--3883",

journal = "European Journal of Organic Chemistry",

issn = "1099-0690",

publisher = "Wiley",

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TY - JOUR

T1 - Stereoselective a-alkylation of fully protected L-serine

AU - Koskinen, Ari M.P.

AU - Saarenketo, Pauli

AU - Straub, Thomas

PY - 2004

Y1 - 2004

N2 - Diastereoselective alkylation of the (2S,4S) and (2R,4S) diastereomers of 3-tert-butyl 4-methyl 2-tert-butyl-1,3-oxazolidine-3,4-dicarboxylate (1a/b) is reported. Formation of both diastereomers of these oxazolidines was achieved by changing the order of protection steps, and their relative and absolute configurations were determined by NOESY spectroscopy. The use of the bulky ring substituent tBu together with Boc as the N-protecting group led to the exclusive formation of only one alkylated diastereomer.

AB - Diastereoselective alkylation of the (2S,4S) and (2R,4S) diastereomers of 3-tert-butyl 4-methyl 2-tert-butyl-1,3-oxazolidine-3,4-dicarboxylate (1a/b) is reported. Formation of both diastereomers of these oxazolidines was achieved by changing the order of protection steps, and their relative and absolute configurations were determined by NOESY spectroscopy. The use of the bulky ring substituent tBu together with Boc as the N-protecting group led to the exclusive formation of only one alkylated diastereomer.

KW - L-serine

KW - NOESY

KW - stereoselective

KW - L-serine

KW - NOESY

KW - stereoselective

KW - L-serine

KW - NOESY

KW - stereoselective

U2 - 10.1002/ejoc.200400207

DO - 10.1002/ejoc.200400207

M3 - Article

SN - 1099-0690

SP - 3879

EP - 3883

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

ER -

Stereoselective a-alkylation of fully protected L-serine

Abstract

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CCDC 230045: Experimental Crystal Structure Determination

Cite this