10.1021/jo500771g.s002
Tapobrata Mitra
Tapobrata
Mitra
Saibal Jana
Saibal
Jana
Sharmila Pandey
Sharmila
Pandey
Prabuddha Bhattacharya
Prabuddha
Bhattacharya
Uttam K. Khamrai
Uttam K.
Khamrai
Anakuthil Anoop
Anakuthil
Anoop
Amit Basak
Amit
Basak
Asymmetric Garratt–Braverman
Cyclization: A
Route to Axially Chiral Aryl Naphthalene–Amino Acid Hybrids
American Chemical Society
2014
diastereoselective
Axially
hybrid
Cyclization
diastereoselectivity
CD spectrum
acid
HybridsWe report
density
Asymmetric
cyclization
activation
Naphthalene
Garratt
synthesis
Chiral
3.48
formation
Aryl
naphthalene
stereogenecity
chiral
energy barrier
yield
Computation
kcal
aryl
M diastereomer
M isomer
2014-06-20 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Asymmetric_Garratt_Braverman_Cyclization_A_Route_to_Axially_Chiral_Aryl_Naphthalene_Amino_Acid_Hybrids/2280937
We report the first example of a
highly diastereoselective Garratt–Braverman
cyclization leading to the synthesis of chiral aryl naphthalene–amino
acid hybrids in excellent yields. The stereogenecity in the amino
acid has induced high diastereoselectivity for the reaction. Computations
based on density functional theory indicated a lower activation free
energy barrier for the <b>M</b> isomer as compared to that for
the <b>P</b> diastereomer (ΔΔ<i>G</i> =
3.48 kcal/mol). Comparison of the recorded CD spectrum of the product
with the calculated one also supported the preferential formation
of the <b>M</b> diastereomer.