Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene: an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes

Inés Alonso; Juan C. Carretero; José L. García Ruano; Luisa M. Martín Cabrejas; Isabel López-Solera; Paul R. Raithby

doi:10.1016/S0040-4039(00)78571-6

Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene: an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes

Inés Alonso
, Juan C. Carretero
, José L. García Ruano
, Luisa M. Martín Cabrejas
, Isabel López-Solera
, Paul R. Raithby

Universidad Autónoma de Madrid
University of Cambridge

Research output: Contribution to journal › Article › peer-review

Abstract

The reactions of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene catalyzed by EtAlCl₂ yields adducts easily desulfinylated into optically pure perhydro-cyclopenta[a]phenanthrenes. The endo- (controlled by CO group) and regio- (controlled by the substituent at C-2 of diene) selectivities of the asymmetric Diels-Alder reaction are complete. The π-facial selectivity is also very high and dependent on both the sulfinyl configuration and the amount of EtAlCl₂ used.

Original language	English
Pages (from-to)	9461-9464
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	50
DOIs	https://doi.org/10.1016/S0040-4039(00)78571-6
Publication status	Published - 12 Dec 1994

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(00)78571-6

Cite this

Alonso, I., Carretero, J. C., García Ruano, J. L., Martín Cabrejas, L. M., López-Solera, I., & Raithby, P. R. (1994). Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene: an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes. Tetrahedron Letters, 35(50), 9461-9464. https://doi.org/10.1016/S0040-4039(00)78571-6

Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene: an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes. / Alonso, Inés; Carretero, Juan C.; García Ruano, José L. et al.
In: Tetrahedron Letters, Vol. 35, No. 50, 12.12.1994, p. 9461-9464.

Research output: Contribution to journal › Article › peer-review

Alonso, I, Carretero, JC, García Ruano, JL, Martín Cabrejas, LM, López-Solera, I & Raithby, PR 1994, 'Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene: an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes', Tetrahedron Letters, vol. 35, no. 50, pp. 9461-9464. https://doi.org/10.1016/S0040-4039(00)78571-6

@article{31d1eb3e5f904a70a4637f47b2423e98,

title = "Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene: an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes",

abstract = "The reactions of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene catalyzed by EtAlCl2 yields adducts easily desulfinylated into optically pure perhydro-cyclopenta[a]phenanthrenes. The endo- (controlled by CO group) and regio- (controlled by the substituent at C-2 of diene) selectivities of the asymmetric Diels-Alder reaction are complete. The π-facial selectivity is also very high and dependent on both the sulfinyl configuration and the amount of EtAlCl2 used.",

author = "In{\'e}s Alonso and Carretero, \{Juan C.\} and \{Garc{\'i}a Ruano\}, \{Jos{\'e} L.\} and \{Mart{\'i}n Cabrejas\}, \{Luisa M.\} and Isabel L{\'o}pez-Solera and Raithby, \{Paul R.\}",

year = "1994",

month = dec,

day = "12",

doi = "10.1016/S0040-4039(00)78571-6",

language = "English",

volume = "35",

pages = "9461--9464",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "50",

}

TY - JOUR

T1 - Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene

T2 - an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes

AU - Alonso, Inés

AU - Carretero, Juan C.

AU - García Ruano, José L.

AU - Martín Cabrejas, Luisa M.

AU - López-Solera, Isabel

AU - Raithby, Paul R.

PY - 1994/12/12

Y1 - 1994/12/12

N2 - The reactions of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene catalyzed by EtAlCl2 yields adducts easily desulfinylated into optically pure perhydro-cyclopenta[a]phenanthrenes. The endo- (controlled by CO group) and regio- (controlled by the substituent at C-2 of diene) selectivities of the asymmetric Diels-Alder reaction are complete. The π-facial selectivity is also very high and dependent on both the sulfinyl configuration and the amount of EtAlCl2 used.

AB - The reactions of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene catalyzed by EtAlCl2 yields adducts easily desulfinylated into optically pure perhydro-cyclopenta[a]phenanthrenes. The endo- (controlled by CO group) and regio- (controlled by the substituent at C-2 of diene) selectivities of the asymmetric Diels-Alder reaction are complete. The π-facial selectivity is also very high and dependent on both the sulfinyl configuration and the amount of EtAlCl2 used.

UR - https://www.scopus.com/pages/publications/0027941647

U2 - 10.1016/S0040-4039(00)78571-6

DO - 10.1016/S0040-4039(00)78571-6

M3 - Article

AN - SCOPUS:0027941647

SN - 0040-4039

VL - 35

SP - 9461

EP - 9464

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

Diels-Alder reaction of (S)-2-p-tolylsulfinyl-2-cyclopentenone with Dane's diene: an efficient approach to the enantioselective preparation of perhydro-cyclopenta[a]phenanthrenes

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this