667587
(7R,10S)-(+)-1-Aza-10-isopropyl-8-oxa-4-thiabicyclo[5.3.0]-2-decanone
97%
Synonym(s):
Gleason chiral auxiliary
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About This Item
Empirical Formula (Hill Notation):
C10H17NO2S
Molecular Weight:
215.31
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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assay
97%
form
solid
mp
142-146 °C
SMILES string
[H][C@@]12CCSCC(=O)N1[C@H](CO2)C(C)C
InChI
1S/C10H17NO2S/c1-7(2)8-5-13-10-3-4-14-6-9(12)11(8)10/h7-8,10H,3-6H2,1-2H3/t8-,10-/m1/s1
InChI key
DCIDQFQEFRCDOM-PSASIEDQSA-N
Application
This chiral lactam auxiliary has been successfully employed in the stereocontrolled synthesis of all carbon quaternary centers. The unique methodology developed by Gleason allows for the creation of either antipode of the product using a single isomer of the auxiliary.[1]
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Azélie Arpin et al.
Organic letters, 8(7), 1359-1362 (2006-03-28)
[reaction: see text] Chiral bicyclic thioglycolate lactams may be prepared in three steps from inexpensive commercial materials. The resulting lactams may be alkylated three times, twice using basic enolization and once using reductive enolization, to form alpha-quaternary carboxylic acid derivatives
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