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The reaction was compatible with electrondonating groups (MeO),
Notes and references
with a similar efficiency (middleꢀleft). The 1ꢀnaphthol can be also
used in the same reaction to obtain an excellent enantioselectivity
but a lower yield (3l, 50%). Other aryl groups, such as 3,5ꢀ
dimethoxyphenol gave a lower yield and enantioselectivities
(bottomꢀright). Interestingly, the use of 3,4ꢀdimethoxyphenol and
2ꢀmethylresorcinol gave an excellent enantioselectivity but a
moderate yield were found for both cases (3n and 3o). The yield of
3n was improved to 50% by using 40 mol% of catalyst 4e. Finally,
a less activated phenol ring, such as 3,5ꢀdimethylphenol, did not
gave the reaction, and only traces of the expected product 3p can be
found in the crude mixture.
a
Departamento de Química Inorgánica (Módulo 7), bDepartamento de
Química Orgánica, Facultad de Ciencias, Universidad Autónoma de
Madrid.
† Electronic Supplementary Information (ESI) available: Experimental
Procedure for synthesis of compounds 3 and Xꢀray data of compound 3h
and 3j (CCDC 902091 and 902092). See DOI: 10.1039/b000000x/
‡ Financial support from Spanish Government (CTQꢀ2009ꢀ12168,
10 SAF2009ꢀ09431) and CAM (programa AVANCAT CS2009/PPQꢀ1634).
J. A. thanks the MICINN for a “Ramon y Cajal” contract.
Cantoblanco,
28049-Madrid
(Spain).
E-mail:
5
1
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40 11 (a) Asymmetric Organocatalysis (Eds.: A. Berkessel, H. Grçger),
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The absolute configuration was unequivocally determined by
Xꢀray diffraction analysis from crystals of compounds 3h and 3j,†
which allowed us to assign their absolute configuration as (1S,2S)
in both cases (Figure 1). This assignment was then used for the
remainder of the compounds 3 depicted in Table 3 and Scheme 2.
45
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Figure 1. Xꢀ Ray analysis of compounds 3h (left) and 3j (right).
In conclusion we have found that chiral transꢀdihydroarylfuran
derivatives can be efficiently synthesized from (Z)ꢀ
bromonitroalkenes and naphthol or phenol derivatives from
moderated to good yield and excellent ee´s by using a squaramide
catalysis. The key of this catalytic system is the neutralization of
the generated HBr by a stequiometric coꢀbase.
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