(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl (R)-4-methylbenzenesulfonimidate
, Marco Colella, Roberta Savina Dibenedetto, Leonardo Degennaro * and Renzo Luisi *Round 1
Reviewer 1 Report
The authors here present the imidation of Andersen's reagent using I(III) reagent. This study features the synthesis of a new chiral sulfonimidate, which can be a reagent for asymmetric synthesis.
Publish with minor revision.
Did the authors test amines other than ammonium carbamate?
Author Response
We are grateful to review 1 for the comment. In our previous works, we disclosed that the transient reactive iodonitrene can be generated by employing a selection of ammonia sources such as ammonium acetate and a solution of ammonia in methanol among others. However, the best results were obtained when ammonium carmabate was used. Therefore, the optimized receipt has been employed in the present paper to access the titled compound from the corresponding sulfinate.
Reviewer 2 Report
This article “(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl-(R)-4-methylben-zenesulfonimidate” reported a stereoselective synthesis of the titled compound via NH-transfer to the corresponding sulfinate by employing hypervalent iodine (DIB) with excellent enantioselectivity. Meanwhile, the authors have developed a novel methodology for the hypervalent iodine-mediated NH-transfer reaction. This report unveiled an asymmetric NH transfer as part of their well-continuing research. The chiral product has been well-characterized with HNMR, CNMR, COSY, HSQC, HRMS, as well as chiral HPLC. The manuscript is well-written and well-organized. Therefore, the reviewer recommends it be published on Molbank.
There are two concerns that should be addressed.
1) In the abstract, IR spectroscopy was mentioned. However, there is no IR described in the manuscript.
2) In Scheme 1, the R4 from the Grignard reagent is incorrectly labeled as R4 in the product.
Author Response
Our reply
We are thankful to review 2 for the comment.
There are two concerns that should be addressed.
1) In the abstract, IR spectroscopy was mentioned. However, there is no IR described in the manuscript.
Our reply
The IR analysis can be found in section 3-material and methods together with NMR characterization, HRMS and the optical rotatory power.
2) In Scheme 1, the R4 from the Grignard reagent is incorrectly labeled as R4 in the product.
Our reply
We are grateful to the reviewer for the suggestion. Scheme 1 has been corrected accordingly.
Typos and language issues corrections:
Evidenced in “track changes” lines 10, 23, 43, 49, 62, 64, 87.
