Diastereoselective 1,3-dipolar cycloadditions with enantiopure azomethine ylids

Enders, Dieter; Meyer, Ilka; Runsink, Jan; Raabe, Gerhard

doi:10.1016/s0040-4020(98)00638-3

Cited by 19 publications

(10 citation statements)

References 16 publications

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“…Other amines whose nitrogen atom is not in a heterocyclic ring, such as systems 109, [176] 110, [177] 111, [178] and 112, [179] have been used as chiral partners in a multicomponent 1,3-dipolar cycloaddition. Their reaction with arenecarbaldehyde or glyoxalate derivatives yields the expected proline derivatives, usually in good yields.…”

Section: Diastereoselective Approachmentioning

confidence: 99%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

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Asymmetric multicomponent reactions involve the preparation of chiral compounds by the reaction of three or more reagents added simultaneously. This kind of addition and reaction has some advantages over classic divergent reaction strategies, such as lower costs, time, and energy, as well as environmentally friendlier aspects. All these advantages, together with the high level of stereoselectivity attained in some of these reactions, will force chemists in industry as in academia to adopt this new strategy of synthesis, or at least to consider it as a viable option. The positive aspects as well as the drawbacks of this strategy are discussed in this Review.

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Section: Diastereoselective Approachmentioning

confidence: 99%

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

2005

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“…The results of the α-alkylation are summarised in Table 3. The configuration of the newly generated stereogenic centre has already been investigated [17,19] and was found to be in agreement with the proposed mechanism for the alkylation of metallated SAMP hydrazones. [14] For the subsequent nucleophilic 1,2-addition to the CN double bond, organocerium reagents were used.…”

Section: Synthesis Of Anti-12-tert-butylsulfanyl Aminesmentioning

confidence: 99%

“…(100), 161 (5), 144 (5), 129 (12), 123 (10), 117 (19), 114 (12), 112 (6), 91 (15), 82 (7), 71 (7), 70 (15), 57 (15), 55 (6), 45 (9). (7), 369 (24), 367 (24), 326 (16), 325 (98), 324 (21), 323 (100), 313 (9), 279 (14), 277 (16), 244 (24), 243 (43), 199 (35), 187 (32), 169 (5), 155 (31), 143 (27), 141 (13), 131 (6), 130 (8), 129 (6), 115 (6), 114 (19), 112 (13), 109 (17), 102 (6), 82 (14), 71 (27), 70 (42), 69 (6), 68 (12), 57 (55), 56 (8), 55 (15), 45 (40). C 19 H 29 BrN 2 OS (413.42): calcd.…”

Section: (2s2s)-(؊)-[2-(tert-butylsulfanyl)-4-methylpentylidene][2-(unclassified

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A Flexible Asymmetric Synthesis of anti‐1,2‐Sulfanyl Amines

Enders¹,

Moll²,

Schaadt³

et al. 2003

Eur J Org Chem

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An efficient and flexible asymmetric synthesis of various protected anti-1,2-sulfanyl amines bearing two adjacent stereogenic centres is described. Key steps are the diastereoselective α-alkylation of α-sulfanylated acetaldehyde-SAMPhydrazones with various electrophiles and subsequent nucleophilic 1,2-addition of organocerium reagents to the hydrazone CN double bond. The resulting hydrazines were converted into the title compounds with excellent diastereo-

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“…While cycloadditions of azomethine ylides to carboncarbon double bond (C=C) are well-known [38][39][40], very few reports have been found where cycloaddition of azomethine ylides with carbonyl double bond are reported [34]. In some cases cycloaddition of azomethine ylides with carbonyl double bond was reported as a side reaction, and not as a synthetic procedure on its own [31].…”

Section: Introductionmentioning

confidence: 99%

Simple and efficient routes to substituted oxazolidine and spiro-oxindole systems by one-pot synthetic strategies

Gayen

Banerji

2014

Monatsh Chem

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Simple and efficient strategies towards the synthesis of substituted spiro-oxindole and oxazolidine systems by one-pot multi-component catalyst-free reactions utilising aryl aldehydes and a-amino acids have been developed. Owing to their complicated structure and ring strain spiro-oxindole moieties are not easily synthesised. In either route 1,3-dipolar cycloadditions involving non-stabilised azomethine ylides as intermediates, generated in situ from amino acids and aldehydes, with the dipolarophile present in the reaction mixture viz. (E)-bnitrostyrene, were utilised. The route to substituted oxazolidines involved cycloaddition to the C=O bond of a second molecule of the aldehyde.

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Diastereoselective 1,3-dipolar cycloadditions with enantiopure azomethine ylids

Cited by 19 publications

References 16 publications

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

Asymmetric Multicomponent Reactions (AMCRs): The New Frontier

A Flexible Asymmetric Synthesis of anti‐1,2‐Sulfanyl Amines

Simple and efficient routes to substituted oxazolidine and spiro-oxindole systems by one-pot synthetic strategies

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