Design and synthesis of chiral N-chloroimidodicarbonates: Application to asymmetric chlorination of silyl enol ethers

Journal of Organic Chemistry

Volumn 72, Issue 13, 2007, Pages 4872-4876

  Hajra, Saumen ^a   Bhowmick, Manishabrata ^a   Maji, Biswajit ^a   Sinha, Debarshi ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINATING AGENTS; CHLOROKETONES; LEWIS ACIDS;

CHIRALITY; CHLORINATION; ENANTIOSELECTIVITY; ETHERS; KETONES; SAMARIUM; SYNTHESIS (CHEMICAL);

CARBONATES;

CHLORINE DERIVATIVE; ETHER DERIVATIVE; LEWIS ACID; N CHLOROIMIDODICARBONATE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHLORINATION; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 34250834349     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070614n     Document Type: Article

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19. 3 was used, only to avoid the presence of unchelated rotamers.
20. Since it showed modest enantioselectivity, no further attempt was made to determine the absolute stereochemistry of chiral α-chloroketones 9.
21. From the TS, the absolute srereochemistry of cyclic α-chloroketone 9a (from 8a) and acyclic α-chloroketones 9c/9d and 9e-g might be predicted as S and R, respectively.