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Tetrahedron Letters

Volumn 25, Issue 18, 1984, Pages 1883-1886

Stereochemical consequences for the Lewis acid mediated additions of allyl and crotyltri-n-butylstannane to chiral β-hydroxyaldehyde derivatives

(2) Keck, Gary E a Abbott, Duain E a

a UNIVERSITY OF UTAH (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000751968 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)90066-8 Document Type: Article

Times cited : (177)

References (16)

1
- 0001057466
- (1984) Tetrahedron Lett. , vol.25 , pp. 265
- Keck¹ Boden²

2
- 84918395641
- G.E. Keck and E.P. Boden, preceding paper in this issue.

3
- 33845554752
- For “one electron” carbon-carbon bond forming reactions using organostannanes, note G.
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 5829
- Keck¹ Yates²

4
- 0001070142
- (1979) Tetrahedron Lett. , pp. 4347
- Johnson¹ Kishi²

5
- 0019780985
- (1981) Tetrahedron Lett. , vol.37 , pp. 3873
- Nagaoka¹ Kishi²

6
- 84918395640
- Full experimental details and a complete discussion of the results described herein will be given in our full paper.

7
- 0002451214
- 6b to describe diastereofacial selectivity (c.f. structures 2 and 3 versus 4 and 5) consistent with this description but without mechanistic implication., and references therein.
- (1977) Nouv. J. Chim. , vol.1 , pp. 61
- Anh¹ Eisenstein²

8
- 33845557437
- 6d, For convenience, abbreviations for diastereofacial selectivity (C or F) and bond formation stereochemistry (E or T) follow the structure numbers in Tables I and II.
- (1981) J. Org. Chem. , vol.46 , pp. 2290
- Heathcock¹ Pirrung² Lampe³ Buse⁴ Young⁵

9
- 84918395639
- 2).

10
- 33847085986
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 7107
- Yamamoto¹ Yatagai² Naruta³ Maruyama⁴

11
- 84918395638
- Other products (corresponding to reverse crotyl addition) are also produced in this case.

12
- 84918395637
- This experiment was performed utilizing “normal” addition, i.e. addition of organostannane to a stirring solution of aldehyde and Lewis acid at −78°.

13
- 84918395636
- This experiment was performed utilizing “inverse” addition, i.e. addition of aldehyde to a stirring solution of organostannane and Lewis acid.

14
- 84918395635
- 2a

15
- 85025748053
- Allylbutyltin halides (CH2CHCH2)SnBu3−nCln (n = 0, 1, 2, 3). Preparation, carbon-13 NMR characterization and allylstannylation ability towards ketones and aldehydes
- and references therein.
- (1980) Journal of Organometallic Chemistry , vol.197 , pp. 45
- Gambaro¹ Peruzzu² Plazzogna³ Tagliavini⁴

16
- 84918395634
- Support of this research by the Alfred P. Sloan Foundation, Eli Lilly and Co., and the National Institutes of Health (through grant ♯GM-28961) is gratefully acknowledged.

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