(S,S)-1-(Phenyl((1′-4-nitrophenyl-ethyl)amino)methyl)-2-naphthol
Round 1
Reviewer 1 Report
In this manuscript Capozzi et al. describe the synthesis and characterization of a novel substrate of the Betti reaction, employing 2-naphthol, benzaldehyde and (S)-1-(4-nitrophenyl)ethylamine as substrates. Per analogy to previous work reported in reference 9, the absolute stereochemistry was assigned to be (S,S). The following corrections are required before publication of the article:
· Line 2 and throughout manuscript: Most common is to report the absolute stereochemistry as (S,S), not as (S, S).
· Line 63: Show the absolute stereochemistry for the reaction scheme, i.e. (S)-1-(4-nitrophenyl)ethylamine and the (S,S)-configuration of the title compound.
· Line 64: (S)-1-(4-nitrophenyl)ethylamine (no space).
· Line 87: Indicate that the values in Table 1 are from reference 9, as these are already reported data.
· Line 97: Was the (R,S)-isomer isolated and characterized? If yes, in which yield? Were NMR data collected that confirm the assignment of the absolute configuration (compare Table 1).
· Line 108: Describe colour/appearance and consistency (solid/crystals?) of the product. How much product (X g, X mmol) was obtained in total?
· Line 116: The calculated molecular mass for [M–H]– C25H21N2O3 is 397.1552, which significantly differs from the reported value of 397.1817. Either HRMS has to be remeasured (positive mode?) or elemental analysis should be provided for the title compound as alternative characterization method.
· Supporting information, p1: Show the absolute configuration of the title compound.
· Supporting information, p2-3: Pick NMR peaks and show that spectra were calibrated to the solvent signal.
Author Response
To the Editor- Molbank.
Manuscript 2072814
Dear Reviewer,
we thank the reviewers for their work and for their suggestions that allowed us to improve our manuscript. Herein, we summed up the modifications that were performed to accomplish to the requests.
(S, S) and (R, S) were corrected in the text to the forms without spaces, that is (S,S) and (R,S).
The absolute stereochemistry was drawn in Scheme 2.
The space was removed in line 64.
As far as the H(1)-NMR data of the (R,S)-stereoisomers and the isolation of this stereoisomer is concerned, we added new text lines (lines 79-86) in the edited version to explain these points.
Colour/appearance of the sample were added. Total mass of the sample was added.
The HRMS of the title compound was recorded again with a recrystallised sample, calibrating carefully the instrument. Now, the difference between the calculated and the found value is 0.001, a satisfactory value.
Supporting Information.
The absolute configuration of the title compound was drawn.
The mark on each NMR spectra were added on the printed spectra.
Author Response File: 
Author Response.pdf
Round 2
Reviewer 1 Report
After careful revision of the manuscript, I fully support publication of the article in its current form.
