The use of chiral sulfides in catalytic asymmetric epoxidation

Aggarwal, Varinder K.; Thompson, A.; Jones, Ray V. H.; Standen, M. C.

doi:10.1016/0957-4166(95)00334-l

Cited by 38 publications

(22 citation statements)

References 17 publications

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“…Initial attempts using 20 mol% sulfide 218 and 10 mol% Rh 2 (OAc) 4 resulted in the synthesis of epoxides in satisfactory yields (58-62%) but enantioselectivity was low (11% ee). Although enantioselectivity was also improved by use of these sulfide catalysts it was still modest and did not exceed 41% ee [216]. When optically active sulfides, which are derived from camphor, are used in the presence of rhodium acetate epoxides of type 202 are formed in good yields and with good diastereomeric ratio (up to d.r.…”

Section: Epoxide Formation From Ylides Prepared By Metal-catalyzed Camentioning

confidence: 99%

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Nucleophilic Addition to CO Double Bonds

Berkessel

Gröger

2005

Asymmetric Organocatalysis

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H CN HO 97 %, 97 % ee (ref. 23) 83 %, >98 % ee (ref. 26) H CN HO 61 %, 91 % ee (ref. 23) H CN HO 76 %, 93 % ee (ref. 23) H 3 CO H CN HO 78 %, 96 % ee (ref. 23) H 3 C H CN HO H 3 C 95 %, 91 % ee (ref. 22) H CN HO H 3 CO 83 %, 97 % ee (ref. 23) H CN HO PhO 97 %, 92 % ee (ref. 23) 84 %, 95 % ee (ref. 26) H CN HO 85 %, 83 % ee (ref. 22) H 3 CO H CN HO 45 %, 84 % ee (ref. 23) OCH 3 H CN HO 90 %, 80 % ee (ref. 22) F 3 C H CN HO 50 %, 89 % ee (ref. 22) N H H 3 C O O H O 76 %, 93 % ee (ref. 22) Scheme 6.2 132 6 Nucleophilic Addition to CbO Double Bonds 1: 83 %, 97 % ee (R ) (ref. 23) 2: 89 %, 56 % ee (S ) (ref. 33) t-Bu H O 91 %, 66 % ee (ref. 33) i-Pr H O 83 %, 64 % ee (ref. 33) H O 98 %, 74 % ee (ref. 33) n-C 5 H 11 H O 93 %, 81 % ee (ref. 33)

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Section: Epoxide Formation From Ylides Prepared By Metal-catalyzed Camentioning

confidence: 99%

“…The Aggarwal group also extended this concept to asymmetric epoxidation [214][215][216]. Initial attempts using 20 mol% sulfide 218 and 10 mol% Rh 2 (OAc) 4 resulted in the synthesis of epoxides in satisfactory yields (58-62%) but enantioselectivity was low (11% ee).…”

Section: Epoxide Formation From Ylides Prepared By Metal-catalyzed Camentioning

confidence: 99%

Nucleophilic Addition to CO Double Bonds

Berkessel

Gröger

2005

Asymmetric Organocatalysis

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“…As metal catalysts, both Cu(acac) 2 and Rh 2 (OAc) 4 were effective at promoting the formation of the sulfonium ylide intermediate. Further studies investigated the use of chiral sulfides such as 62 (Scheme 51a) [126][127][128].…”

Section: Epoxidationmentioning

confidence: 99%

Sulfur-Based Ylides in Transition-Metal-Catalysed Processes

et al. 2018

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Traditionally employed in the synthesis of small ring systems and rearrangement chemistry, sulfur-based ylides occupy a unique position in the toolbox of the synthetic organic chemist. In recent years a number of pioneering researchers have looked to expand the application of these unorthodox reagents through the use of transition metal catalysis. The strength and flexibility of such a combination have been shown to be of key importance in developing powerful novel methodologies. This chapter summarises recent developments in transition metal-catalysed sulfonium/sulfoxonium ylide reactions, as well as providing a historical perspective. In overviewing the successes in this area, the authors hope to encourage others into this growing field.

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“…Sulfides 5 and 6 became our target and Alison prepared these and tested them in the catalytic cycle with rhodium acetate. 31 They both worked and gave only moderate (but interestingly opposite) enantioselectivity in formation of stilbene oxide (Scheme 12). I was quite surprised at the level of enantioselection shown by sulfide 5 as there is very little steric difference between the two faces of the corresponding ylide.…”

Section: Scheme 11mentioning

confidence: 99%