All Photos(1)

458538

Sigma-Aldrich

(3S-cis)-(+)-Tetrahydro-3,7a-diphenylpyrrolo[2,1-b]oxazol-5(6H)-one

98%

Empirical Formula (Hill Notation):
C18H17NO2
CAS Number:
Molecular Weight:
279.33
MDL number:
PubChem Substance ID:

assay

98%

optical activity

[α]20/D +113°, c = 1 in chloroform

mp

82-85 °C (lit.)

SMILES string

O=C1CC[C@]2(OC[C@@H](N12)c3ccccc3)c4ccccc4

Application

Chiral bicyclic lactams such as this are useful templates for the asymmetric synthesis of a variety of natural and unnatural products. High levels of asymmetric induction have been obtained in cycloadditions, alkylations, conjugate additions, annulations, and dihydroxylations.

Certificate of Analysis

Certificate of Origin

Andres, C.J. et al.
Tetrahedron Letters, 60, 3189-3189 (1995)
Brengel, G.P. Meyers, A.I.
The Journal of Organic Chemistry, 61, 3230-3230 (1996)
Romo, D. Meyers, A.I.
Tetrahedron, 47, 9503-9503 (1991)
Munchhoff, M.J. Meters, A.I.
The Journal of Organic Chemistry, 60, 7086-7086 (1995)
Meyers, A.I. et al.
The Journal of Organic Chemistry, 60, 4359-4359 (1995)

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