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Please login or sign up for a free trial to access the full content.27.1.3.2.1 Method 1: Reaction of Sulfonium Ylides with Aldehydes and Ketones
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Aggarwal, V.; Richardson, J., Science of Synthesis, (2004) 27, 70.
In 1958, Johnson and LaCount reported the first example of the reaction of a sulfur ylide with an aldehyde to give an epoxide.[12] In a seminal work four years later,[230] Corey and Chaykovsky reported the general application of sulfonium ylide 101 with a wide range carbonyl compounds to give epoxides 133 (Scheme 70); this addition–elimination reaction has become known as the Corey–Chaykovsky reaction and is clearly analogous to the epoxidation of carbonyl compounds using sulfoxonium ylides (see Section 27.1.2.2.1). The epoxidation of carbonyl compounds in this way is one of the most common applications of such species in organic synthesis. The epoxidation of such carbonyl species with sulfonium ylides represents a complimentary method to the Wittig alkenation followed by alkene oxidation that might otherwise be employed to achieve the same overall transformation.
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Mee ee eee eeeeeeeeee ee eeeeeeeeeeeee ee eee eeeeeeee eeee, 88 eee 888 eeeee eeee eeeeeeeeeeeee eeeeeeeeeeeee ee eeeeeeeee eeee eeeeeeee eeeeeeeee. Mee eeeeeee, eeeeeeee ee eeeeeeeeeeeeeeeeeee eeeeeeeee (88) eeee 8-eeee-eeeeeeeeeeeeeeeeee eeeee eeeeeeeeeee eee eeeeeeeeeeeeeeeee eeee eeeeee eee-eeeeeee eee-88, eeeeeee eeeeeeee ee eeeeeeeeeeeeeeeee eeeeeeeee (888) eeeee eee eeeee-eeeeee eeeee-88 eeeeeeeeeeeee (Meeeee 88).[88]
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Meeeee 88 Meeeee ee Meeeeeeeeeeeeeee ee Meeeeeee ee Meeeeeeeeeee eeee Meeeee-Meeeeeeeee Meeeeeeee Meeeee[888]
Meeeeeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeeee eeee eeeeeeeee eeeeee eee eeeeeeeeee eeeeeeeeee ee eeee eee eeeeeeee eee eeeee eeeeeeee eeeeeeee eee eeeeeee eeeeeeeee eee ee eeeeeeeeeee eee eeeeee eeee eeee eeee ee eee eeeeee ee eee eeeeeeeee eeeeeeee eeeeeeeeee eeeeee eee ee eee eeeeee eeeee eeeeeeee ee eee eeeeeeee eeeeeeeee eeeeeeeeeeee.[888] Meee eeeeeeeeee eeeeee, eeee ee eeeee eeee eeeee eeeeeeeeeee eeeeee, eeeeeee eeeeeeeeee eeeeeeeeee eeeeeeee ee eeeeeeeee eee eeee eeee eeeeeeeeeee eeeee-eeeeeeee eee eee eeeee ee eeeeeeee eeeeeeee eeeeeeee. Mee eeeee ee eeeeeeeee eeee eee ee eeeeeeeee eeee eeeeeeee ee eeee eeeeee ee eeeeeeeeeeee.
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Meeeee 88 Meeeeeee-Meee Meeeeeeeee ee ee Meeeeeeeeeee Meeeeee[888]
Me eee eeeeeeee ee eeeeee eeeeeeeeeeeeeeeee eeeeeeeee (888), eee eeeeeeeeeeeee eeeeeee eee eeeeeee eeee eeeeeee eee eeeeeeeeee eeeeeeeeeee ee eeee ee eeeeeee eeeeeee.[888,888] Meeeeeeeeeeeeeeeeee eeeeeeeee (88) eeee eee eeeeeee eee eeee eeeeeeeeeeeeee eee ee eeeeeee ee eeeeee eeeeeee (eee Meeeeee 88.8.8.8.8). Me eeeee eee eeeee eeeeeeee ee eee eeeeeeeeeee eeeee eeeeeee ee eeee eeeeeeeeeee eee eeee eeeeee eeee eeeeeee.
References
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88-8, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 8888.
- 8.Meeeee-Meee, (8888) M 88e, 888.
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